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

Authors: Biswas, Atanu; ALVES, CARLUCIO - Universidade Estadual Do Ceara; TREVISAN, MARIA - Universidade Federal Do Ceara (UFC); DA SILVA, ROSEANE - Universidade Federal Do Ceara (UFC); FURTADO, ROSELAYNE - Embrapa; Liu, Zengshe - Kevin; Cheng, Huai

Submitted to: Frontiers of Chemical Science and Engineering
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/16/2016
Publication Date: 8/25/2016
Publication URL: http://handle.nal.usda.gov/10113/5642498
Citation: Biswas, A., Alves, C.R., Trevisan, M.T.S., da Silva, R.L.E., Furtado, R.F., Liu, Z., Cheng, H.N. 2016. Synthesis of a cardanol-amine derivative using an ionic liquid catalyst. Frontiers of Chemical Science and Engineering. 10(3):425-431.

Interpretive Summary: Most of the current industrial chemicals originate from petroleum stock, which is limited in the world's reserves. There is a need to use agricultural raw materials because they are renewable, potentially cheaper, and environmentally friendly. The interest intensified during the last decade due to governmental regulations and environmental sustainability goals. We have developed a novel solvent and catalyst-free green pathway to incorporate amine group into cardanol, a phenolic lipid obtained from cashew nut shell liquid (CNSL). The CNSL is a byproduct of cashew nut processing. Currently, only a fraction of the cardanol obtained from cashew nut processing is used in the industrial field. In view of the availability and low cost of cardanol, it is useful to develop new reaction pathways and new polymers. The reaction reported in this work was carried out with a small amount of an ionic liquid. No byproducts were produced, and the ionic liquid was recovered and recycled. Impact: New materials prepared in this paper perhaps can be used as an antioxidant or heat stabilizer in lubricants, coatings, cosmetics, and agricultural chemicals. The materials further modified with formaldehyde can be formulated into adhesives, curing agents for epoxy resins, fuel cell materials, or water purification media. Furthermore, the aromatic ring can bind to fragrance or drug ingredients, and can be modified to be a convenient carrier for fragrance or drug molecules. In view of the multiple potential uses, industrial chemical manufacturers will benefit from this discovery.

Technical 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 can be further reacted to form thermosetting resins.