Frontiers of Chemical Science and Engineering >
Synthesis of a cardanol-amine derivative using an ionic liquid catalyst
Received date: 19 Mar 2016
Accepted date: 16 Jun 2016
Published date: 23 Aug 2016
Copyright
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.
Key words: cardanol; epoxidation; aminohydrin; aniline; ionic liquid; aniline-formaldehyde
Atanu Biswas , Carlucio R. Alves , Maria T. S. Trevisan , Roseane L. E. da Silva , Roselayne F. Furtado , Zengshe Liu , H. N. Cheng . Synthesis of a cardanol-amine derivative using an ionic liquid catalyst[J]. Frontiers of Chemical Science and Engineering, 2016 , 10(3) : 425 -431 . DOI: 10.1007/s11705-016-1581-3
1 |
Balachandran V S, Jadhav S R, Vemula P K, John G. Recent advances in cardanol chemistry in a nutshell: From a nut to nanomaterials. Chemical Society Reviews, 2013, 42(2): 427–438
|
2 |
Mele G, Vasapollo G. Fine chemicals and new hybrid materials from cardanol. Mini-Reviews in Organic Chemistry, 2008, 5(3): 243–253
|
3 |
Vasapollo G, Mele G, Del Sole R. Cardanol-based materials as natural precursors for olefin metathesis. Molecules (Basel, Switzerland), 2011, 16(12): 6871–6882
|
4 |
Voirin C, Caillol S, Sadavarte N V, Tawade B V, Boutevin B, Wadgaonkar P P. Functionalization of cardanol: Towards biobased polymers and additives. Polymer Chemistry, 2014, 5(9): 3142–3162
|
5 |
Jaillet F, Darroman E, Ratsimihety A, Auvergne R, Boutevin B, Caillol S. New biobased epoxy materials from cardanol. European Journal of Lipid Science and Technology, 2014, 116(1): 63–73
|
6 |
Kanehashi S, Yokoyama K, Masuda R, Kidesaki T, Nagai K, Miyakoshi T. Preparation and characterization of cardanol-based epoxy resin for coating at room temperature curing. Journal of Applied Polymer Science, 2013, 130(4): 2468–2478
|
7 |
Huang K, Zhang Y, Li M, Lian J, Yang X, Xia J. Preparation of a light color cardanol-based curing agent and epoxy resin composite: Cure-induced phase separation and its effect on properties. Progress in Organic Coatings, 2012, 74(1): 240–247
|
8 |
Sultania M, Rai J, Srivastava D. Modeling and simulation of curing kinetics for the cardanol-based vinyl ester resin by means of non-isothermal DSC measurements. Materials Chemistry and Physics, 2012, 132(1): 180–186
|
9 |
Suresh K I, Kishanprasad V S. Synthesis, structure, and properties of novel polyols from cardanol and developed polyurethanes. Industrial & Engineering Chemistry Research, 2005, 44(13): 4504–4512
|
10 |
Kim Y H, An E S, Park S Y, Song B K. Enzymatic epoxidation and polymerization of cardanol obtained from a renewable resource and curing of epoxide-containing polycardanol. Journal of Molecular Catalysis. B, Enzymatic, 2007, 45(1-2): 39–44
|
11 |
Chen J, Nie X, Liu Z, Mi Z, Zhou Y. Synthesis and application of polyepoxide cardanol glycidyl ether as biobased polyepoxide reactive diluent for epoxy resin. ACS Sustainable Chemistry & Engineering, 2015, 3(6): 1164–1171
|
12 |
Rao B S, Palanisamy A. Synthesis of biobased low temperature curable liquid epoxy, benzoxazine monomer system from caardanol: Thermal and viscoelastic properties. European Polymer Journal, 2013, 49(8): 2365–2376
|
13 |
Plechkova N V, Seddon K R. Applications of ionic liquids in the chemical industry. Chemical Society Reviews, 2008, 37(1): 123–150
|
14 |
Chiappe C, Pieraccini D. Ionic liquids: Solvent properties and organic reactivity. Journal of Physical Organic Chemistry, 2005, 18(4): 275–297
|
15 |
Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chemical Reviews, 1999, 99(8): 2071–2084
|
16 |
Kilpeläinen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos D S. Dissolution of wood in ionic liquids. Journal of Agricultural and Food Chemistry, 2007, 55(22): 9142–9148
|
17 |
Rogers R D, Seddon K R. Ionic liquids—Solvents of the future? Science, 2003, 302(5646): 792–793
|
18 |
Sheldon R. Catalytic reactions in ionic liquids. Chemical Communications, 2001, 23: 2399–2407
|
19 |
Biswas A, Sharma B K, Doll K M, Erhan S Z, Willett J L, Cheng H N. Synthesis of an amine-oleate derivative using an ionic liquid catalyst. Journal of Agricultural and Food Chemistry, 2009, 57(18): 8136–8141
|
20 |
Darroman E, Bonnot L, Auvergne R, Boutevin B, Caillol S. New aromatic amine based on cardanol giving new biobased epoxy networks with cardanol. European Journal of Lipid Science and Technology, 2015, 117(2): 178–189
|
21 |
Bishop R R. The use of aniline-formaldehyde resins as curing agents for epoxide resins. Journal of Applied Chemistry, 1956, 6(6): 256–260
|
22 |
Maity T, Samanta B C, Dalai S, Banthia A K. Curing study of epoxy resin by new aromatic amine functional curing agents along with mechanical and thermal evaluation. Materials Science and Engineering, 2007, 464(1-2): 38–46
|
23 |
Chuang C, Chao L, Huang Y, Hsieh T, Chuang H, Lin S, Ho K. Synthesis and characterization of a novel proton-exchange membrane for fuel cells operating at high temperatures and low humidities. Journal of Applied Polymer Science, 2008, 107(6): 3917–3924
|
24 |
Knop A, Pilato L A. Phenolic Resins, Chemistry, Applications and Performance, Future Directions. Berlin: Springer-Verlag, 1985
|
25 |
Gaca K Z, Parkinson J A, Lue L, Sefcik J. Equilibrium speciation in moderately concentrated formaldehyde-methanol-water solutions investigated using 13C and 1H nuclear magnetic resonance spectroscopy. Industrial & Engineering Chemistry Research, 2014, 53(22): 9262–9271
|
26 |
Tomita B, Hatono S. Urea-formaldehyde resins. III. Constitutional characterization by 13C Fourier transform NMR spectroscopy. Journal of Polymer Science: Polymer Chemistry Edition, 1978, 16: 2509–2525
|
27 |
Mustata F, Bicu I. Epoxy aniline formaldehyde resins modified with resin acids. Polimery, 2001, 46: 534–539
|
28 |
Panahi H A, Zadeh M S, Tavangari S, Moniri E, Ghassemi J. Nickel adsorption from environmental samples by ion imprinted aniline-formaldehyde polymer. Iran Journal of Chemistry and Chemical Engineering, 2012, 31: 35–44
|
29 |
Kalal H S, Hoveidi H, Thagiof M, Pakizevand N, Almasian M R, Firoozzare M A. Pre-concentration and determination of platinum (IV) in water samples using chelating resin by inductively coupled plasma atomic emission spectroscopy (ICP-AES). International Journal of Environmental of Research, 2012, 6: 739–750
|
30 |
Kumar P A, Ray M, Chakraborty S. Hexavalent chromium removal from wastewater using aniline formaldehyde condensate coated silica gel. Journal of Hazardous Materials, 2007, 143(1-2): 24–32
|
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