Methods of making pyrrolidones

Werpy, Todd; Frye, Jr., John G.; Wang, Yong; Zacher, Alan H.

Methods of making pyrrolidones

Patent · Mon Mar 15 23:00:00 EST 2004

OSTI ID:1174772

Werpy, Todd; Frye, Jr., John G.; Wang, Yong; Zacher, Alan H.

The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC06-76RL01830

Assignee:: Battelle Memorial Institute (Richland, WA)

Patent Number(s):: 6,706,893

Application Number:: 10/280,577

OSTI ID:: 1174772

Country of Publication:: United States

Language:: English

References (7)

An Integrated Process for the Production of Chemicals from Biologically Derived Succinic Acid Nghiem, Nhuan; Davison, Brian H.; Donnelly, Mark I. Chemicals and Materials from Renewable Resources, p. 160-173 https://doi.org/10.1021/bk-2001-0784.ch013	book	February 2001
New method for the preparation of N-aryl- and N-alkylpyrrolidones and some of their properties Kukalenko, S. S.; Gracheva, N. A. Chemistry of Heterocyclic Compounds, Vol. 7, Issue 6 https://doi.org/10.1007/BF00476817	journal	June 1971
Modified ZSM-5 Catalysts for the Synthesis of Five- and Six-Membered Heterocyclic Compounds Subba Rao, Yarlagadda V.; Kulkarni, Shivanand J.; Subrahmanyam, Machiraju The Journal of Organic Chemistry, Vol. 59, Issue 14 https://doi.org/10.1021/jo00093a035	journal	July 1994
N-Methylation of amides, lactams, and ureas Auerbach, Joseph.; Zamore, McFord.; Weinreb, Steven M. The Journal of Organic Chemistry, Vol. 41, Issue 4 https://doi.org/10.1021/jo00866a038	journal	February 1976
N-Alkylation of Lactams with Phase Transfer Catalyst Takahata, Hiroki; Hashizume, Torahiko; Yamazaki, Takao HETEROCYCLES, Vol. 12, Issue 11 https://doi.org/10.3987/R-1979-11-1449	journal	January 1979
N-Methyl-2-pyrrolidone. Yano, Yoshinori Journal of Synthetic Organic Chemistry, Japan, Vol. 41, Issue 9 https://doi.org/10.5059/yukigoseikyokaishi.41.880	journal	January 1983
Catalytic Hydrogenation of Acetophenone Over Ruthenium Catalysts Červený, Libor; Dobrovolná, Zuzana; Bělohlav, Zdeněk Collection of Czechoslovak Chemical Communications, Vol. 61, Issue 5 https://doi.org/10.1135/cccc19960764	journal	January 1996

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References (7)

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