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Thermal degradation of flame-retardant compounds derived from castor oil

A renewable biomaterial

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Abstract

Castor oil is a non-edible plant oil produced in a large quantity annually. It is a triglyceride of primarily (approximately 90%) ricinoleic acid. The acid residues contain both a hydroxyl group and a double bond which permit ready functionalization. The hydroxyl group may be converted to phosphorus esters of varied structure while the unsaturation readily undergoes addition of bromine. Derivatives of castor oil containing phosphorus, bromine, or phosphorus and bromine have been prepared and fully characterized using spectroscopic and thermal methods. The thermal stability and mode of degradation for these compounds have been assessed using thermogravimetry and infrared spectroscopy. The primary mode of degradation for the phosphorus esters is elimination of the corresponding phosphorus acid (phosphates more readily than phosphonates). Brominated castor oil undergoes thermally induced dehydrobromination at relatively modest temperatures and this promotes dehydration (at temperatures well below that required for dehydration of unmodified castor oil). Brominated phosphorus esters of castor oil undergo degradation initiated by dehydrobromination.

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Acknowledgements

Diphenylchlorophosphate was generously provided by ICL-IP America, Inc.

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Authors and Affiliations

  1. Center for Applications in Polymer Science, Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, MI, 48859-0001, USA

    Bob A. Howell & Eric A. Ostrander

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  1. Bob A. Howell
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  2. Eric A. Ostrander
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Correspondence to Bob A. Howell.

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Howell, B.A., Ostrander, E.A. Thermal degradation of flame-retardant compounds derived from castor oil. J Therm Anal Calorim 138, 3961–3975 (2019). https://doi.org/10.1007/s10973-019-08355-w

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  • DOI: https://doi.org/10.1007/s10973-019-08355-w

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