Transforming Sugarcane Bagasse into Bioplastics via Homogeneous Modification with Phthalic Anhydride in Ionic Liquid

Chen, Mingjie; Shi, Qingshan

doi:10.1021/acssuschemeng.5b00685

Cited by 45 publications

(28 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A further increase in the dosage of glutaric anhydride from 40 to 50 mmol/g resulted in an unexpected decrease in the substituted hydroxyl content from 4.48 (B4) to 3.96 (B5) mmol/g, corresponding to a PS decrease from 31.33% to 27.69%. These results implied that changing glutaric anhydride dosage could regulate PS of bagasse samples, consistent with the previous study [ 22 ]. As shown in Table 2 , unmodified bagasse was insoluble in water and common organic solvents, while glutaric anhydride could be dissolved in the selected solvents.…”

Section: Resultssupporting

confidence: 92%

Esterification Mechanism of Bagasse Modified with Glutaric Anhydride in 1-Allyl-3-methylimidazolium Chloride

et al. 2017

View full text Add to dashboard Cite

The esterification of bagasse with glutaric anhydride could increase surface adhesion compatibility and the surface of derived polymers has the potential of immobilizing peptides or proteins for biomedical application. Due to its complicated components, the esterification mechanism of bagasse esterified with glutaric anhydride in ionic liquids has not been studied. In this paper, the homogenous esterification of bagasse with glutaric anhydride was comparatively investigated with the isolated cellulose, hemicelluloses, and lignin in 1-allyl-3-methylimidazolium chloride (AmimCl) to reveal the reaction mechanism. Fourier transform infrared (FT-IR) indicated that the three components (cellulose, hemicelluloses, and lignin) were all involved in the esterification. The percentage of substitution (PS) of bagasse was gradually improved with the increased dosage of glutaric anhydride (10–40 mmol/g), which was primarily attributed to the increased esterification of cellulose and hemicelluloses. However, the PS fluctuation of lignin led to a decrease in the PS of bagasse at high glutaric anhydride dosage (50 mmol/g). The esterification reactivity of bagasse components followed the order of lignin > hemicelluloses > cellulose. The esterification mechanism was proposed as a nucleophilic substitution reaction. Nuclear magnetic resonance (NMR) analysis indicated that lignin aliphatic hydroxyls were prior to be esterified, and primary hydroxyls were more reactive than secondary hydroxyls in cellulose and hemicelluloses.

show abstract

Section: Resultssupporting

confidence: 92%

Esterification Mechanism of Bagasse Modified with Glutaric Anhydride in 1-Allyl-3-methylimidazolium Chloride

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Additionally, ILs can be tailored to meet the required application due to its designability [ 24 ]. Recently, ILs as efficient solvents have been widely studied [ 25 , 26 ], and the derivatization of bagasse in ILs has been reported [ 27 , 28 , 29 ]. There also have been some literatures on the homogeneous esterification between bagasse and maleic anhydride in ILs [ 21 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Structural Changes of Bagasse dusring the Homogeneous Esterification with Maleic Anhydride in Ionic Liquid 1-Allyl-3-methylimidazolium Chloride

et al. 2018

View full text Add to dashboard Cite

Abstract:The maleation of bagasse could greatly increase the compatibility between bagasse and composite matrixes, and the percentage of substitution (PS) of bagasse maleates could be regulated in the homogeneous system. However, due to the complicated components and the linkages of bagasse, it was difficult to control the reaction behaviors of each component. In this paper, the detailed structural changes of bagasse during the homogeneous maleation in ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl) were comparatively investigated with the three main components (cellulose, hemicelluloses, and lignin) from bagasse. The PS of the maleated bagasse was 12.52%, and the PS of the maleated cellulose, hemicelluloses, and lignin were 13.50%, 10.89%, and 14.03%, respectively. Fourier translation infrared (FT-IR) and NMR analyses confirmed that the three main components were all involved in the homogeneous maleation. 1 H-13 C HSQC analysis indicated that the predominant monoesterification of cellulose, diesterification of hemicelluloses and lignin, and the degradation of the three main components simultaneously occurred. Besides, the quantitative analysis from 1 H-13 C HSQC revealed the relative PS of reactive sites in each component. 31 P NMR results showed that the reactivity of lignin aliphatic hydroxyls was higher than that of phenolic ones, and the reactivity of phenolic hydroxyls followed the order of p-hydroxyphenyl hydroxyls > guaiacyl hydroxyls > syringyl hydroxyls.

show abstract

“…Previously, many researches have been conducted on the esterification of SCB for different application purposes. For example, thermoformable materials could be synthesized by the esterification of SCB with succinic anhydride, using as an excellent cation exchanger for the adsorption of heavy metal ions, such as Cu 2+ , Ni 2+ , Cr 3+ and Fe 3+ [ 18 , 19 ]; oil absorption materials were also prepared using acetic anhydride (AA) as esterifying reagent and the acetylated SCB presented excellent oil sorption capacity, with 1.9 times higher than that of commercial polypropylene oil sorbent [ 20 ]; and bioplastic films with mechanical properties compared to cellulose esters were prepared from SCB by esterification and subsequent solution casting [ 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Mechanocatalytic Solvent-Free Esterification of Sugarcane Bagasse

Zhang

Zhu

et al. 2018

Polymers

View full text Add to dashboard Cite

Esterification is a versatile way to produce the derivatives of lignocellulose with developed properties. However, the traditional heterogeneous esterification of lignocellulose suffered from the drawbacks of low efficiency, additional reaction medium and heating. In the present study, an efficient method was developed to produce the functionalized sugarcane bagasse (SCB) by ball milling without any additional solvents and heating. The effects of pulverization time, rotation speed, the kind of linear chain anhydrides, the ratio of anhydrides to SCB, with or without pyridine catalyst and the dosage of catalyst were investigated on weight percent gain (WPG) of SCB esters. The results indicated that the high efficiency of this mechanocatalystic esterification was probably due to the destroyed crystalline structure and the promoted penetration of the esterifying reagent onto SCB bulk caused by ball milling. The maximum WPG of SCB acetate, propionate and butyrate reached 33.3%, 33.6% and 32.4%, respectively. The physicochemical structure of the esterified SCB was characterized with Fourier transform infrared spectra (FT-IR), solid state cross-polarized magic angle spinning 13C nuclear magnetic resonance (CP/MAS 13C-NMR), X-ray diffraction (XRD), scanning electron microscopy (SEM) and thermogravimetric analysis (TGA). The direct evidence of the esterification occurrence was provided with FT-IR and solid-state CP/MAS 13C-NMR. The thermal stability of SCB increased upon the mechanocatalytic esterification. The results implied that the relatively homogeneous modification was achieved with this semi-homogeneous esterification method by ball milling.

show abstract

Transforming Sugarcane Bagasse into Bioplastics via Homogeneous Modification with Phthalic Anhydride in Ionic Liquid

Cited by 45 publications

References 23 publications

Esterification Mechanism of Bagasse Modified with Glutaric Anhydride in 1-Allyl-3-methylimidazolium Chloride

Esterification Mechanism of Bagasse Modified with Glutaric Anhydride in 1-Allyl-3-methylimidazolium Chloride

Structural Changes of Bagasse dusring the Homogeneous Esterification with Maleic Anhydride in Ionic Liquid 1-Allyl-3-methylimidazolium Chloride

Mechanocatalytic Solvent-Free Esterification of Sugarcane Bagasse

Contact Info

Product

Resources

About