Soybean oil as feedstock for the synthesis and characterization of a carnauba substitute and a study of the structure-function relationships

Tao Fei; Darren Jarboe; Tong Wang

Journal of Industrial and Engineering Chemistry, Vol.57, 416-423, January, 2018

DOI10.1016/j.jiec.2017.08.050 Export Citation

Soybean oil as feedstock for the synthesis and characterization of a carnauba substitute and a study of the structure-function relationships

Tao Fei¹, Darren Jarboe², and Tong Wang^{1, 3, †}

¹Department of Food Science and Human Nutrition, Iowa State University, Ames, IA 50011, USA
²Center for Crops Utilization Research, USA
³Center for Crops Utilization Research

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A soybean oil-based carnauba substitute was developed, and structure.function relationships were established. Amide derivatives of saturated fatty acid showed higher hardness and melting point than ester derivatives having the same chain length. Increasing chain length using diacids increased hardness. The cinnamic ring was confirmed to contribute to surface shininess and smoothness. The addition of long-chain fatty alcohols increased the hardness of a C52 (carbon chain length of 52) diester. Overall, a material consisted of C52 polyamide (76.3 wt%), C38 diamide (11.3 wt%), and C29 diamide with a ring structure (12.4 wt%) showed comparable hardness and surface properties as carnauba wax.

Keywords:Cinnamic acid;Fully hydrogenated soybean oil;Monoamide;Diamide;Polyamide;Soybean oil-based carnauba wax substitute

[References]

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Wang L, Wang T, J. Am. Oil Chem. Soc., 84, 1149 (2007)
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[1] Kelley MJ, 1941. Hard wax substitute. U.S. Patent 2,356,408.

[2] Feairheller SH, Bistline RG, Bilyk A, Dudley RL, Kozempel MF, Haas MJ, J. Am. Oil Chem. Soc., 71, 863 (1994)

[3] Vandenburg LE, Wilder EA, J. Am. Oil Chem. Soc., 47, 514 (1970)

[4] Doan CD, To CM, De Vrieze M, Lynen F, Danthine S, Brown A, Dewettinck K, Ratel A, Food Chem., 214, 717 (2017)

[5] Basson I, Reynhardt EC, J. Phys. D-Appl. Phys., 21, 1429 (1988)

[6] Waksmundzka-Hajnos M, Sherma J, High Performance Liquid Chromatogra-phy in Phytochemical Analysis. Chapter 5, (2011) p. 92, ISBN: 978-1-4200-9260-8.

[7] Wang L, Wang T, J. Am. Oil Chem. Soc., 84, 1149 (2007)

[8] Vandenburg LE, Wilder EA, J. Am. Oil Chem. Soc., 44, 659 (1967)

[9] Ferdous K, Uddin MR, Mondal SK, Khan M, Islam M, Preparation and characterization of biodiesel from karanja (pongamia pinnata) oil by different methods, International Conference on Mechanical Engineering and Renewable Energy (2011), doi:http://dx.doi.org/10.13140/2.1.2098.9766.

[10] Yildiz Y, Dasgupta M, Am. J. Anal. Chem., 7, 611 (2016)

[11] Attard P, Stiernstedt J, Rutland M, J. Phys. Conf. Ser., 61, 51 (2007)

[12] Duong CT, Park S, Chang J, Lee S, Surface roughness and frictional coefficient of hip implant using atomic force microscopy, 55th Annual Meeting of the Orthopaedic Research Society Poster (2009).

[13] Abes M, Narine S, Chem. Phys. Lipids, 149, 14 (2007)

[14] Raghunanan L, Narine S, J. Phys. Chem. B, 117, 14753 (2013)

[15] Yao L, Lio J, Wang T, Jarboe D, J. Am. Oil Chem. Soc., 90, 1063 (2013)

[16] Callinan T, Crimi J, Mcgee H, Parks A, Schwartz P, 1964. Synthetic wax substitutes for carnauba wax and transfer ink compositions containing such substitutes. US Patent 3,129,104 A.

[17] Mohamed C, Labat M, Patel B, Garcia J, Int. J. Syst. Evol. Microbiol., 51, 2049 (2001)

[18] Holser RA, Mitchell TR, Harry-O’Kuru RE, Vaughn SF, Walter E, Himmelsbach D, J. Am. Oil Chem. Soc., 85, 347 (2008)