Sustainable separation of bio-based cadaverine based on carbon dioxide capture by forming carbamate

Li, Hui; Xu, Xu; Tan, Weimin; Lü, Xu; He, Feng; Xu, Sheng; Tian, Weilong; Chen, Kequan; Li, Ganlu; Ouyang, Pingkai; Liu, Yaozong; Liang, Ruiyuan

doi:10.1039/d0ra08564b

Cited by 4 publications

(2 citation statements)

References 44 publications

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“…Our team is committed to researching biobased PDI. In our previous study, sugar from biomass was used as the raw material to produce 1,5-pentanediamine through fermentation, and PDI was subsequently synthesized from 1,5-pentanediamine using the phosgene method. , The resulting PDI adhesive exhibited excellent adhesion . In this study, biobased PDI was used as the raw material and 2-hydroxypropyl-trimethylisooctanoic acid ammonium salt (TMR) was employed as the catalyst to synthesize biobased PDI trimers.…”

Section: Introductionmentioning

confidence: 99%

Reducing High-Molecular-Weight Oligomers in Biobased Pentamethylene Diisocyanate Trimers

Yang,

Hu,

et al. 2024

Ind. Eng. Chem. Res.

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New biobased pentamethylene diisocyanate (PDI) trimers have received increasing attention because of their high biochar content and excellent performance in coatings. However, their viscosity can affect the curing rate and application of coatings. This study aimed to decrease the viscosity of PDI trimers by reducing the content of high-molecular-weight oligomers. Using 2-hydroxypropyltrimethylisooctanoic acid ammonium salt as a catalyst at a dosage of 0.3 wt ‰, the catalyst was added in two batches at 80 °C, with an interval of 15 min between each addition. The reaction lasted for 90 min until the NCO conversion rate reached 15.71%. The resulting PDI trimer contained a high-molecular-weight oligomer content of 0.53% and exhibited a viscosity of 1425 mPa·s. Furthermore, to address the significant increase in the content of high-molecular-weight oligomers during the later stages of the reaction, a novel reaction pathway was proposed to elucidate the generation of high-molecular-weight oligomers from those with lower molecular weights. Gaussian calculations were employed to determine the reaction energy barriers of different pathways, confirming that the reaction pathway for synthesizing a heptamer from two trimers and one monomer is possible. Moreover, this study provides insights into methods for mitigating the increase in high-molecular-weight oligomers in the later stages of the reaction.

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Section: Introductionmentioning

confidence: 99%

Reducing High-Molecular-Weight Oligomers in Biobased Pentamethylene Diisocyanate Trimers

Yang,

Hu,

et al. 2024

Ind. Eng. Chem. Res.

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“…Our group has created a complete, mature technology route for biobased PDI. First, we fermented biomass sugar to form l -lysine, then converted l -lysine into 1,5-pentanediamine or cadaverine by lysine decarboxylase, and finally synthesized PDI using 1,5-pentanediamine as the raw material. ,− We also found that PDI shows excellent adhesion performance when applied to adhesives . In this work, we used PDI as a raw material to synthesize the PDI isocyanurate trimer and allophanate-modified PDI isocyanurate trimer (PDI-T-M) by introducing butanediol, then removed the unreacted free PDI monomer to prepare PDI isocyanurate curing agents, and finally prepared 2K-PU coatings to verify the coating performances.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Monomer Removal, Modification, and Coating Performances of Biobased Pentamethylene Diisocyanate Isocyanurate Trimers

Zeng

Yang

Tang

et al. 2022

Ind. Eng. Chem. Res.

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The new green biobased pentamethylene diisocyanate (PDI) trimer curing agent has lower-life-cycle carbon emissions than the petrochemical-based hexamethylene diisocyanate (HDI) trimer curing agent, and its performance is similar to that of petrochemical-based products. This work focused on the synthesis, allophanate modification, free PDI monomer removal, and coating performances of PDI isocyanurate trimers. The results showed that optimal synthesis of PDI isocyanurate trimers used 2-hydroxypropyltrimethylisooctanoate ammonium salt (TMR) as a catalyst with 0.4 wt ‰ added and a reaction time of 120 min. The best free PDI monomer removal by molecular distillation used a removal temperature of 130 °C, a scraper speed of 350 rpm, and a feed rate of 3 mL·min–1, with two total removals. Self-made and allophanate-modified PDI isocyanurate trimers showed high values in physical and chemical properties. The water resistance, acid and alkali resistance, and aging resistance of the self-made and allophanate-modified PDI isocyanurate trimers were similar to or even better than those of petrochemical-based HDI products. These results indicate the application potential of biobased PDI-trimer curing agents.

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Exploration of the rapid growth of high-molecular-weight oligomers in the later stage of diisocyanate self-polymerization

Yang,

Hu,

Zhao

et al. 2024

Polymer

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Sustainable separation of bio-based cadaverine based on carbon dioxide capture by forming carbamate

Abstract: Cadaverine carbamate, capturing the self-released carbon dioxide from the decarboxylation of l-lysine, is the green and sustainable separation of bio-based cadaverine.

Cited by 4 publications

References 44 publications

Reducing High-Molecular-Weight Oligomers in Biobased Pentamethylene Diisocyanate Trimers

Reducing High-Molecular-Weight Oligomers in Biobased Pentamethylene Diisocyanate Trimers

Synthesis, Monomer Removal, Modification, and Coating Performances of Biobased Pentamethylene Diisocyanate Isocyanurate Trimers

Exploration of the rapid growth of high-molecular-weight oligomers in the later stage of diisocyanate self-polymerization

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