Oxyalkylation of gambier tannin—Synthesis and characterization of ensuing biobased polyols

Arbenz, Alice; Avérous, Luc

doi:10.1016/j.indcrop.2015.01.073

Cited by 46 publications

(67 citation statements)

References 32 publications

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“…On the other hand, T max increased with the GT/BO ratio from 150 to 192 C. At high GT content, several graed chains grow at the same time from the numerous OH groups. 32 The reaction time is longer for oxybutylation compared to oxypropylation, 42 and it decreases with the increase in GT content. 32 Compared to the oxypropylation of tannins, it is well-know that BO is less reactive than PO.…”

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

“…12,13,34 In Table 4, the results show that the formation of HOMO decreased with the increase in the GT/BO ratio. 42 However, for polyols from the 10/90 and 20/80 series, HOMO cannot be isolated. 34 This method was also used on oxypropylated tannin.…”

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

“…These values are close to those obtained for fossil-based polyols used industrially in the synthesis of polyurethanes. 12,13,42 GT and oxybutylated polyol derivates were analyzed by TGA. This reduction is linked to the increase in the molar masses by graed polymerization.…”

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

“…43 For high carbohydrate content (>10%), the degradation temperature decreased in comparison with pure tannin. 42 Tannin derivatives showed lower thermal stability due to the degradation of graed polyether chains, linked to the thermal sensitivity of ether groups.…”

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and characterization of fully biobased aromatic polyols – oxybutylation of condensed tannins towards new macromolecular architectures

Arbenz

Avérous

2014

RSC Adv.

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For the first time, different tannins were oxybutylated to obtain aromatic and fully biobased polyols. The main interest in using 1,2-butylene oxide (BO) instead of e.g., propylene oxide is because BO can be easily biobased and biosynthesized from biomass. BO can be obtained by epoxidation of butane, produced from biobased butanol, synthesized by biotechnological means. The oxybutylation was carried out using potassium hydroxide as a catalyst, in a high-pressure batch reactor, without solvent, in agreement with the main principles of green chemistry. Firstly, different biobased aromatic polyols were synthesized from gambier tannin (Uncaria gambir) and fully characterized. To better understand the conditions and mechanisms of the synthesis, the influence of the tannin/BO ratio was assessed through the evolution of the hydroxyl content, homopolymer content, molar mass distributions and the corresponding viscosities. In addition, the thermal properties were evaluated to better understand the final molecular architectures. Secondly, selected conditions of synthesis were applied to other types of tannins from pine (Pinus pinaster), mimosa (Acacia mearnsii) and quebracho (Schinopsis balansae and Schinopsis lorentzii). The corresponding results were compared to extend this study. For all tannins, the number and length of the grafted chains were carefully characterized. Great variations in reactivity have been found between the different botanical sources. Tailor-made, fully biobased and controlled aromatic macropolyols can be obtained by modulating the main parameters of the oxybutylation reaction and the type of botanical tannin source.

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Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

Section: Synthesis and Characterization Of Oxybutylated Gambier Tannimentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and characterization of fully biobased aromatic polyols – oxybutylation of condensed tannins towards new macromolecular architectures

Arbenz

Avérous

2014

RSC Adv.

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“…The resulting polyols are liquid mixtures of oxypropylenated biomass, homopolymer of propylene oxide, and unreacted biomass (Evtiouguina et al 2002). This method of polyol production was investigated by many research groups which incorporated into the process various types of biomass such as, coffee grinds (Evtiouguina et al 2002), sugar beet pulp (Pavier and Gandini 2000), gambier tannin (Arbenz and Averous 2015), soy hulls (Rosa et al 2015), rapeseed cake residue (Briones et al 2010), and olive stones (Matos et al 2010).…”

Section: Introductionmentioning

confidence: 99%

Biopolyols obtained via crude glycerol-based liquefaction of cellulose: their structural, rheological and thermal characterization

et al. 2016

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In this work lignocellulose biomass liquefaction was used to produce biopolyols suitable for the manufacturing of rigid polyurethane foams. In order to better evaluate the mechanism of the process, pure cellulose was applied as a raw material. The effect of time and temperature on the effectiveness of liquefaction and the parameters of resulting biopolyols were characterized. The prepared materials were analyzed in terms of their chemical structure, rheology, thermal and oxidative stability, and basic physical and mechanical properties that are important from the point of view of polyurethane manufacturing. The optimal parameters for the biopolyol production with a 94 % yield were achieved at 150°C for a 6-h reaction duration. The obtained polyols were characterized by the hydroxyl number of 643 mg KOH/g and enhanced thermal and oxidative stability compared to the polyols obtained at lower temperatures, which is associated with the altered mechanism of liquefaction. The results of rheological tests, analyzed with the use of Ostwald-de Waele and Herschel Bulkley models, revealed that the prepared biopolyols can be classified as pseudoplastic fluids with the viscosity values similar to those of commercially available products. Rigid foams obtained via partial substitution of petrochemical polyol with prepared biobased one were characterized by slightly increased apparent density and average cell size comparing to unmodified materials. The best mechanical performance was observed for the sample containing 35 wt% of biopolyol in the polyol mixture, which indicates a synergistic effect between the applied polyols. The applied modification delayed thermal degradation of foams due to changes in thermal decomposition process. In conclusion, the presented work confirms that lignocellulose biomass liquefaction can be successfully applied as a manufacturing method of polyols later used in the production of polyurethanes.

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Tannins: A Resource to Elaborate Aromatic and Biobased Polymers

Arbenz

Avérous

2016

Biodegradable and Biobased Polymers for Environmental and Biomedical Applications

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Oxyalkylation of gambier tannin—Synthesis and characterization of ensuing biobased polyols

Cited by 46 publications

References 32 publications

Synthesis and characterization of fully biobased aromatic polyols – oxybutylation of condensed tannins towards new macromolecular architectures

Synthesis and characterization of fully biobased aromatic polyols – oxybutylation of condensed tannins towards new macromolecular architectures

Biopolyols obtained via crude glycerol-based liquefaction of cellulose: their structural, rheological and thermal characterization

Tannins: A Resource to Elaborate Aromatic and Biobased Polymers

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