Open Access
Polymers, volume 14, issue 22, pages 4973
Synthesis of Biobased Hydroxyl-Terminated Oligomers by Metathesis Degradation of Industrial Rubbers SBS and PB: Tailor-Made Unsaturated Diols and Polyols
Manuel Burelo
1
,
Selena Gutiérrez
2
,
Cecilia D. Treviño-Quintanilla
1
,
Jorge A Cruz Morales
2
,
Araceli Martínez
3
,
Salvador López Morales
4
Publication type: Journal Article
Publication date: 2022-11-17
General Chemistry
Polymers and Plastics
Abstract
Biobased hydroxyl-terminated polybutadiene (HTPB) was successfully synthesized in a one-pot reaction via metathesis degradation of industrial rubbers. Thus, polybutadiene (PB) and poly(styrene-butadiene-styrene) (SBS) were degraded via metathesis with high yields (>94%), using the fatty alcohol 10-undecen-1-ol as a chain transfer agent (CTA) and the second-generation Grubbs–Hoveyda catalyst. The identification of the hydroxyl groups (-OH) and the formation of biobased HTPB were verified by FT-IR and NMR. Likewise, the molecular weight and properties of the HTPB were controlled by changing the molar ratio of rubber to CTA ([C=C]/CTA) from 1:1 to 100:1, considering a constant molar ratio of the catalyst ([C=C]/Ru = 500:1). The number average molecular weight (Mn) ranged between 583 and 6580 g/mol and the decomposition temperatures between 134 and 220 °C. Moreover, the catalyst optimization study showed that at catalyst loadings as low as [C=C]/Ru = 5000:1, the theoretical molecular weight is in good agreement with the experimental molecular weight and the expected diols and polyols are formed. At higher ratios than those, the difference between theoretical and experimental molecular weight is wide, and there is no control over HTPB. Therefore, the rubber/CTA molar ratio and the amount of catalyst play an important role in PB degradation and HTPB synthesis. Biobased HTPB can be used to synthesize engineering design polymers, intermediates, fine chemicals, and in the polyurethane industry, and contribute to the development of environmentally friendly raw materials.
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Burelo M. et al. Synthesis of Biobased Hydroxyl-Terminated Oligomers by Metathesis Degradation of Industrial Rubbers SBS and PB: Tailor-Made Unsaturated Diols and Polyols // Polymers. 2022. Vol. 14. No. 22. p. 4973.
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Burelo M., Gutiérrez S., Treviño-Quintanilla C. D., Cruz Morales J. A., Martínez A., López Morales S. Synthesis of Biobased Hydroxyl-Terminated Oligomers by Metathesis Degradation of Industrial Rubbers SBS and PB: Tailor-Made Unsaturated Diols and Polyols // Polymers. 2022. Vol. 14. No. 22. p. 4973.
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TY - JOUR
DO - 10.3390/polym14224973
UR - https://doi.org/10.3390/polym14224973
TI - Synthesis of Biobased Hydroxyl-Terminated Oligomers by Metathesis Degradation of Industrial Rubbers SBS and PB: Tailor-Made Unsaturated Diols and Polyols
T2 - Polymers
AU - Burelo, Manuel
AU - Gutiérrez, Selena
AU - Treviño-Quintanilla, Cecilia D.
AU - Cruz Morales, Jorge A
AU - Martínez, Araceli
AU - López Morales, Salvador
PY - 2022
DA - 2022/11/17 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 4973
IS - 22
VL - 14
SN - 2073-4360
ER -
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@article{2022_Burelo,
author = {Manuel Burelo and Selena Gutiérrez and Cecilia D. Treviño-Quintanilla and Jorge A Cruz Morales and Araceli Martínez and Salvador López Morales},
title = {Synthesis of Biobased Hydroxyl-Terminated Oligomers by Metathesis Degradation of Industrial Rubbers SBS and PB: Tailor-Made Unsaturated Diols and Polyols},
journal = {Polymers},
year = {2022},
volume = {14},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {nov},
url = {https://doi.org/10.3390/polym14224973},
number = {22},
pages = {4973},
doi = {10.3390/polym14224973}
}
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Burelo, Manuel, et al. “Synthesis of Biobased Hydroxyl-Terminated Oligomers by Metathesis Degradation of Industrial Rubbers SBS and PB: Tailor-Made Unsaturated Diols and Polyols.” Polymers, vol. 14, no. 22, Nov. 2022, p. 4973. https://doi.org/10.3390/polym14224973.