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Origins of Life and Evolution of Biospheres

, Volume 49, Issue 4, pp 199–211 | Cite as

Imidazolium-Catalyzed Synthesis of an Imidazolium Catalyst

  • Arthur L. WeberEmail author
  • Andro C. Rios
Prebiotic Chemistry

Abstract

The chemistry of imidazolium-catalyzed imidazolium synthesis was studied as part of an effort to develop a plausible prebiotic synthesis of a small catalytic molecule capable of catalyzing its own synthesis. Specifically, we investigated the one-pot 1-ethyl-3-methylimidazolium acetate (EMIM-Ac) catalyzed synthesis of 1,3-dibutyl-4,5-difuryl-imidazolium acetate (DBDFIM-Ac) from furfural, n-butylamine, formaldehyde, and acetic acid at 80 °C. Liu et al. (2012) had previously demonstrated the first reaction of the synthetic process, the EMIM-Ac catalyzed benzoin condensation of furfural that yields furoin. Our early studies established the second reaction of the synthetic process, the multicomponent reaction of furoin, n-butylamine, formaldehyde, and acetic acid that yields the imidazolium salt, DBDFIM-Ac. Studies of the complete two-reaction process that uses furfural for the synthesis of DBDFIM-Ac showed that the highest yield of DBDFIM-Ac was obtained when the mole ratio of n-butylamine, formaldehyde, and acetic acid relative to furfural was respectively (0.5:0.25:0.25:1.0-furfural), or one-half of the stoichiometric ratio (1.0:0.5:0.5:1.0-furfural). A time course study of the process showed transient formation of furoin, the obligatory reaction intermediate. DBDFIM-Ac and the imidazolium side product, 1,3-dibutyl-4,5-trifuryl-imidazolium acetate (DBTFIM-Ac), were stable under the reaction conditions. Imidazolium products (DBDFIM and DBTFIM) and the furoin intermediate were not formed in control reactions (80 °C, 24 h) in which EMIM catalyst was either absent or replaced with an equal volume of acetonitrile or DMF. The imidazolium product, DBDFIM-Ac, was shown to catalyze the synthesis of structurally similar 1,3-dipentyl-4,5-difuryl-imidazolium acetate (DPDFIM-Ac) from furfural, n-pentylamine, formaldehyde, and acetic acid at 80 °C.

Keywords

Origins of life Prebiotic Imidazolium catalysis Benzoin condensation Catalytic feedback Reflexive catalysis Maillard reaction 

Notes

Acknowledgements

The authors thank Esther Varon for technical assistance in this study. This investigation was supported by a grant (NNX15AL19G) from the Exobiology Program of the National Aeronautics and Space Administration. ACR was supported by Exobiology Program grant, NNH17ZDA001N-EXO.

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.SETI InstituteAmes Research CenterMoffett FieldUSA
  2. 2.Center for the Emergence of LifeNASA Ames Research CenterMoffett FieldUSA
  3. 3.Blue Marble Space InstituteAmes Research CenterMoffett FieldUSA

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