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High Performance Polyhexahydrotriazine (PHT) Thermoset for the Synthesis of Furanics

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Abstract

Highly active, environmental friendly thermosets, polyhexahydrotriazines (PHTs) were prepared through the condensation of aromatic diamines and paraformaldehyde. The sulfonic acid-derived PHT possesses that both Brønsted base and acidic sites have been realized as a potential material in the dehydration of biomass (glucose/fructose) to 5-hydroxymethylfurfural (HMF) at low temperature. This thermoset is degradable at high temperatures (> 80 °C) in the presence of aqueous solution of glucose/fructose with the generation of oxidized products of HMF and consequently produced furan-amine adducts. Moreover, the highly active PHT can be separated at lower temperatures (< 80 °C) with recyclability and found that its activity is declining after each cycle. This thermoset material can be used as an alternative to plastic material which is not degradable even thermally. In addition, PHTs were characterized successfully by various techniques such as PXRD, FT-IR, SEM, BET, and TGA analysis.

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Data Availability

All the data including characterization, HPLC and relevant is available with corresponding author.

Abbreviations

DFF:

2,5-diformyl furan

DMF:

dimethylformamide

DMSO:

dimethyl sulfoxide

FFCA:

5-formyl-2-carboxylic acid

FDCA:

2,5-furan dicarboxylic acid

HMF:

5-hydroxymethylfurfural

HMFCA:

5-hydroxymethyl-2-furancarboxylic acid

PHT:

polyhexahydrotriazine

HT:

hydrotriazine

FTIR:

Fourier transformation infrared spectroscopy

HPLC:

high-performance liquid chromatography

PXRD:

powdered X-ray crystallography

SEM:

scanning electron microscopy

TGA:

thermo gravimetric analysis

BJH:

Barrett-Joyner-Halenda

BET:

Brunauer Emmett and Teller

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Acknowledgements

The authors thank Council of Scientific and Industrial Research and IOE-BHU for the financial support.

Funding

This work was supported by CSIR under the scheme CSIR-01(2968)/19/EMR-II and IOE-BHU (6032) incentive grant for the research faculty.

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Authors and Affiliations

  1. Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, India

    Akanksha Rai, Rama Jaiswal, Manisha Pandey & Kalluri V. S. Ranganath

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  1. Akanksha Rai
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  2. Rama Jaiswal
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  3. Manisha Pandey
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  4. Kalluri V. S. Ranganath
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Contributions

AR conducted the literature search and preparation and characterization of PHTs. MP conducted the synthesis of PHTs and critically revised the work. RJ conducted the biomass degradation reactions and HPLC analysis. KVSR monitored the research work.

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Correspondence to Kalluri V. S. Ranganath.

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Rai, A., Jaiswal, R., Pandey, M. et al. High Performance Polyhexahydrotriazine (PHT) Thermoset for the Synthesis of Furanics. Bioenerg. Res. 16, 507–516 (2023). https://doi.org/10.1007/s12155-022-10453-x

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