Synthesis of a cardanol-amine derivative using an ionic liquid catalyst

doi:10.1007/s11705-016-1581-3

Front. Chem. Sci. Eng.

2016, Vol. 10

Issue (3) : 425-431 https://doi.org/10.1007/s11705-016-1581-3

RESEARCH ARTICLE

Synthesis of a cardanol-amine derivative using an ionic liquid catalyst

Atanu Biswas^1,^*(

),Carlucio R. Alves²,Maria T. S. Trevisan³,Roseane L. E. da Silva³,Roselayne F. Furtado⁴,Zengshe Liu¹,H. N. Cheng^5,^*(

)

¹. USDA Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL 61604, USA
². Chemistry Department, State University of Ceará, Itaperi Campus, 60740-020, Fortaleza-CE, Brazil
³. Chemistry Department, Federal University of Ceará, Pici Campus, 60455-760, Fortaleza-CE, Brazil
⁴. Embrapa Tropical Agroindustry, Rua Dra. Sara Mesquita, Planalto Pici, 60511-110, Fortaleza-CE, Brazil
⁵. USDA Agricultural Research Service, Southern Regional Research Center, New Orleans, LA 70124, USA

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Abstract

Cardanol is a biobased raw material derived from cashew nut shell liquid. In order to extend its utility, new derivatives and additional applications are useful. In this work cardanol was first epoxidized, and a novel aniline derivative prepared from it under mild reaction conditions with the help of an ionic liquid catalyst. The reaction chemistry was studied by using nuclear magnetic resonance. The resulting aminohydrin adduct showed antioxidant property and should also be a useful synthon for further reactions. As an example, the aminohydrin was shown to undergo a condensation reaction with formaldehyde to form a prepolymer, which could be further reacted to form thermosetting resins.

Keywords cardanol epoxidation aminohydrin aniline ionic liquid aniline-formaldehyde

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Fund:

Corresponding Author(s): Atanu Biswas,H. N. Cheng

Just Accepted Date: 08 July 2016 Online First Date: 02 August 2016 Issue Date: 23 August 2016

Cite this article:

Atanu Biswas,Carlucio R. Alves,Maria T. S. Trevisan, et al. Synthesis of a cardanol-amine derivative using an ionic liquid catalyst[J]. Front. Chem. Sci. Eng., 2016, 10(3): 425-431.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-016-1581-3
https://academic.hep.com.cn/fcse/EN/Y2016/V10/I3/425

Fig.1 Scheme 1Formation of cardanol epoxide (reaction 1) and amination (reaction 2) in the presence of an ionic liquid (IL)

Fig.2 ¹H NMR spectra of cardanol and increasing levels of epoxidation: (a) cardanol with assignments of the triene protons, (b) sample E1, (c) sample E2, and (d) sample E3 in Table 1

Tab.1 Examples of cardanol epoxidation under different experimental conditions^a)

Fig.3 ¹³C NMR spectra of cardanol and its derivatives: (a) cardanol; (b) cardanol epoxide sample E3, where two large olefinic peaks (*) are found at 133.1 and 117.5 ppm; (c) cardanol aminohydrin sample A1, where the aniline peaks (N) are assigned; (d) reaction product of cardanol aminohydrin and formaldehyde sample F1. Note that E= residual ethyl acetate; S= solvent, CDCl₃

Fig.4

Fig.5 (a) PDSC curves for PAO 8 solution with (blue) and without (red) cardanol aminohydrin (upper plot); (b) Onset of oxidation temperature (measured by PDSC) as a function of the cardanol aminohydrin additive (sample A1) concentration in PAO 8 solution (lower plot)

Fig.6 Scheme 2Formation of cardanol-containing aniline-formaldehyde resin

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