nach oben

Erschienen in:

21.03.2020 | Original Research

Green method for preparation of cellulose nanocrystals using deep eutectic solvent

verfasst von: Michael A. Smirnov, Maria P. Sokolova, Dmitry A. Tolmachev, Vitaly K. Vorobiov, Igor A. Kasatkin, Nikolay N. Smirnov, Anastasya V. Klaving, Natalya V. Bobrova, Natalia V. Lukasheva, Alexander V. Yakimansky

Erschienen in: Cellulose | Ausgabe 8/2020

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

An environment-friendly method for obtaining cellulose nanocrystals (CNC) using deep eutectic solvents (DES) was developed. Formation of highly crystalline CNC with average particle dimensions 20 × 100 × 700 nm was confirmed with SEM and AFM. Molecular dynamics simulations demonstrated that the hydrogen bond interactions of the cellulose hydroxyl groups with the urea C=O group and with the chloride ions were the key factors of the destruction of MCC particles in the process of solvation. The type of cellulose crystal structure (I_β) and the high degree of crystallinity (about 80% according to Segal method) were preserved during treatment with DES. The ability of the prepared CNC to act as a reinforcing filler was tested by introduction of them into the chitosan-based films plasticized with DES. It was found that addition of 2 wt% of CNC led to an increase in the strength of the films from 11.4 up to 20.4 MPa with a simultaneous increase in the elongation at break.

Graphic abstract

Vorheriger Artikel Tomato plant residue as new renewable source for cellulose production: extraction of cellulose nanocrystals with different surface functionalities

Nächster Artikel Role of solvent exchange in dispersion of cellulose nanocrystals and their esterification using fatty acids as solvents

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Nur mit Berechtigung zugänglich

Abraham MJ, Murtola T, Schulz R et al (2015) GROMACS: high performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX 1–2:19–25. https://doi.org/10.1016/J.SOFTX.2015.06.001 CrossRef

Amde M, Liu J-F, Pang L (2015) Environmental application, fate, effects, and concerns of ionic liquids: a review. Environ Sci Technol 49:12611–12627. https://doi.org/10.1021/acs.est.5b03123 CrossRefPubMed

Amin KNM, Annamalai PK, Morrow IC, Martin D (2015) Production of cellulose nanocrystals via a scalable mechanical method. RSC Adv 5:57133–57140. https://doi.org/10.1039/C5RA06862B CrossRef

Armelin E, Pérez-Madrigal MM, Alemán C, Diaz DD (2016) Current status and challenges of biohydrogels for applications as supercapacitors and secondary batteries. J Mater Chem A 4:8952–8968. https://doi.org/10.1039/C6TA01846G CrossRef

Bai W, Holbery J, Li K (2009) A technique for production of nanocrystalline cellulose with a narrow size distribution. Cellulose 16:455–465. https://doi.org/10.1007/s10570-009-9277-1 CrossRef

Bajkacz S, Adamek J (2017) Evaluation of new natural deep eutectic solvents for the extraction of isoflavones from soy products. Talanta 168:329–335. https://doi.org/10.1016/j.talanta.2017.02.065 CrossRefPubMed

Cao L, Yuan D, Fu X, Chen Y (2018) Green method to reinforce natural rubber with tunicate cellulose nanocrystals via one-pot reaction. Cellulose 25:4551–4563. https://doi.org/10.1007/s10570-018-1877-1 CrossRef

Chi K, Catchmark JM (2018) Improved eco-friendly barrier materials based on crystalline nanocellulose/chitosan/carboxymethyl cellulose polyelectrolyte complexes. Food Hydrocoll 80:195–205. https://doi.org/10.1016/j.foodhyd.2018.02.003 CrossRef

Decaen P, Rolland-Sabaté A, Guilois S et al (2017) Choline chloride vs choline ionic liquids for starch thermoplasticization. Carbohydr Polym 177:424–432. https://doi.org/10.1016/j.carbpol.2017.09.012 CrossRefPubMed

Deng F, Li M-C, Ge X et al (2017) Cellulose Nanocrystals/poly(methyl methacrylate) nanocomposite films: effect of preparation method and loading on the optical, thermal, mechanical, and gas barrier properties. Polym Compos 38:E137–E146. https://doi.org/10.1002/pc.23875 CrossRef

dos Santos FA, Iulianelli GCV, Tavares MIB (2017) Effect of microcrystalline and nanocrystals cellulose fillers in materials based on PLA matrix. Polym Test 61:280–288. https://doi.org/10.1016/j.polymertesting.2017.05.028 CrossRef

Essmann U, Perera L, Berkowitz ML et al (1995) A smooth particle mesh Ewald method. J Chem Phys 103:8577–8593. https://doi.org/10.1063/1.470117 CrossRef

Feng Q, Hou D, Zhao Y et al (2014) Electrospun regenerated cellulose nano fibrous membranes surface- grafted with polymer chains/brushes via the atom transfer radical polymerization method for catalase immobilization. ACS Appl Mater Interfaces 6:20958–20967. https://doi.org/10.1021/am505722g CrossRefPubMed

French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21:885–896. https://doi.org/10.1007/s10570-013-0030-4 CrossRef

French AD, Santiago Cintrón M (2013) Cellulose polymorphy, crystallite size, and the Segal Crystallinity Index. Cellulose 20:583–588. https://doi.org/10.1007/s10570-012-9833-y CrossRef

Galvis-Sánchez AC, Sousa AMM, Hilliou L et al (2016) Thermo-compression molding of chitosan with a deep eutectic mixture for biofilms development. Green Chem 18:1571–1580. https://doi.org/10.1039/C5GC02231B CrossRef

Hirota M, Tamura N, Saito T, Isogai A (2010) Water dispersion of cellulose II nanocrystals prepared by TEMPO-mediated oxidation of mercerized cellulose at pH 4.8. Cellulose 17:279–288. https://doi.org/10.1007/s10570-009-9381-2 CrossRef

Hoover WG (1985) Canonical dynamics: equilibrium phase-space distributions. Phys Rev A 31:1695–1697. https://doi.org/10.1103/PhysRevA.31.1695 CrossRef

Kabanov VA (ed) (1977) Enciklopedija polimerov, vol 3. Sovetskaya Encyclopedia, Moscow

Kony D, Damm W, Stoll S, Van Gunsteren WF (2002) An improved OPLS-AA force field for carbohydrates. J Comput Chem 23:1416–1429. https://doi.org/10.1002/jcc.10139 CrossRefPubMed

Kostritskii AY, Tolmachev DA, Lukasheva NV, Gurtovenko AA (2017) Molecular-level insight into the interaction of phospholipid bilayers with cellulose. Langmuir 33:12793–12803. https://doi.org/10.1021/acs.langmuir.7b02297 CrossRefPubMed

Lee CM, Kubicki JD, Fan B et al (2015) Hydrogen-bonding network and OH stretch vibration of cellulose: comparison of computational modeling with polarized IR and SFG spectra. J Phys Chem B 119:15138–15149. https://doi.org/10.1021/acs.jpcb.5b08015 CrossRefPubMed

Leung ACW, Hrapovic S, Lam E et al (2011) Characteristics and properties of carboxylated cellulose nanocrystals prepared from a novel one-step procedure. Small 7:302–305. https://doi.org/10.1002/smll.201001715 CrossRefPubMed

Li J, Wei X, Wang Q et al (2012) Homogeneous isolation of nanocellulose from sugarcane bagasse by high pressure homogenization. Carbohydr Polym 90:1609–1613. https://doi.org/10.1016/j.carbpol.2012.07.038 CrossRefPubMed

Li X, Feng Y, Chu G et al (2018) Directly and quantitatively studying the interfacial interaction between SiO 2 and elastomer by using peak force AFM. Compos Commun 7:36–41. https://doi.org/10.1016/j.coco.2017.12.006 CrossRef

Ling Z, Edwards JV, Guo Z et al (2019) Structural variations of cotton cellulose nanocrystals from deep eutectic solvent treatment: micro and nano scale. Cellulose 26:861–876. https://doi.org/10.1007/s10570-018-2092-9 CrossRef

Liu Y, Guo B, Xia Q et al (2017) Efficient cleavage of strong hydrogen bonds in cotton by deep eutectic solvents and facile fabrication of cellulose nanocrystals in high yields. ACS Sustain Chem Eng. https://doi.org/10.1021/acssuschemeng.7b00954 CrossRefPubMedPubMedCentral

Lukasheva NV, Tolmachev DA (2016) Cellulose nanofibrils and mechanism of their mineralization in biomimetic synthesis of hydroxyapatite/native bacterial cellulose nanocomposites: molecular dynamics simulations. Langmuir 32:125–134. https://doi.org/10.1021/acs.langmuir.5b03953 CrossRefPubMed

Lynam JG, Kumar N, Wong MJ (2017) Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density. Bioresour Technol. https://doi.org/10.1016/j.biortech.2017.04.079 CrossRefPubMed

Man Z, Muhammad N, Sarwono A et al (2011) Preparation of cellulose nanocrystals using an ionic liquid. J Polym Environ 19:726–731. https://doi.org/10.1007/s10924-011-0323-3 CrossRef

Mao H, Wei C, Gong Y et al (2019) Mechanical and water-resistant properties of eco-friendly chitosan membrane reinforced with cellulose nanocrystals. Polym (Basel) 11:166. https://doi.org/10.3390/polym11010166 CrossRef

Maréchal Y, Chanzy H (2000) The hydrogen bond network in I_β cellulose as observed by infrared spectrometry. J Mol Struct 523:183–196. https://doi.org/10.1016/S0022-2860(99)00389-0 CrossRef

Marín-Silva DA, Rivero S, Pinotti A (2019) Chitosan-based nanocomposite matrices: development and characterization. Int J Biol Macromol 123:189–200. https://doi.org/10.1016/j.ijbiomac.2018.11.035 CrossRefPubMed

Miao J, Yu Y, Jiang Z, Zhang L (2016) One-pot preparation of hydrophobic cellulose nanocrystals in an ionic liquid. Cellulose 23:1209–1219. https://doi.org/10.1007/s10570-016-0864-7 CrossRef

Mondal S (2017) Preparation, properties and applications of nanocellulosic materials. Carbohydr Polym 163:301–316. https://doi.org/10.1016/j.carbpol.2016.12.050 CrossRefPubMed

Mostofian B, Smith JC, Cheng X (2014) Simulation of a cellulose fiber in ionic liquid suggests a synergistic approach to dissolution. Cellulose 21:983–997. https://doi.org/10.1007/s10570-013-0018-0 CrossRef

Mukesh C, Mondal D, Sharma M, Prasad K (2014) Choline chloride-thiourea, a deep eutectic solvent for the production of chitin nanofibers. Carbohydr Polym 103:466–471. https://doi.org/10.1016/j.carbpol.2013.12.082 CrossRefPubMed

Nosé S (1984) A molecular dynamics method for simulations in the canonical ensemble. Mol Phys 52:255–268. https://doi.org/10.1080/00268978400101201 CrossRef

Parrinello M, Rahman A (1981) Polymorphic transitions in single crystals: a new molecular dynamics method. J Appl Phys 52:7182–7190. https://doi.org/10.1063/1.328693 CrossRef

Ren H, Chen C, Wang Q et al (2016) The properties of choline chloride-based deep eutectic solvents and their performance in the dissolution of cellulose. BioResources 11:5435–5451. https://doi.org/10.15376/biores.11.2.5435-5451 CrossRef

Rovera C, Ghaani M, Santo N et al (2018) Enzymatic hydrolysis in the green production of bacterial cellulose nanocrystals. ACS Sustain Chem Eng 6:7725–7734. https://doi.org/10.1021/acssuschemeng.8b00600 CrossRef

Samarov AA, Smirnov MA, Sokolova MP, Toikka AM (2018a) Liquid–liquid equilibrium data for the system N-Octane + Toluene + DES at 293.15 and 313.15 K and atmospheric pressure. Theor Found Chem Eng 52:262–267. https://doi.org/10.1134/S0040579518020148 CrossRef

Samarov AA, Smirnov MA, Toikka AM, Prikhodko IV (2018b) Study of deep eutectic solvent on the base choline chloride as entrainer for the separation alcohol-ester systems. J Chem Eng Data 63:1877–1884. https://doi.org/10.1021/acs.jced.7b00912 CrossRef

Sambasivarao SV, Acevedo O (2009) Development of OPLS-AA force field parameters for 68 unique ionic liquids. J Chem Theory Comput 5:1038–1050. https://doi.org/10.1021/ct900009a CrossRefPubMed

Segal L, Creely JJ, Martin AE, Conrad CM (1959) An empirical method for estimating the degree of crystallinity of native cellulose using the X-Ray diffractometer. Text Res J 29:786–794. https://doi.org/10.1177/004051755902901003 CrossRef

Sirviö JA, Visanko M, Liimatainen H (2015) Deep eutectic solvent system based on choline chloride-urea as a pre-treatment for nanofibrillation of wood cellulose. Green Chem 17:3401–3406. https://doi.org/10.1039/C5GC00398A CrossRef

Sirviö JA, Visanko M, Liimatainen H (2016) Acidic Deep eutectic solvents as hydrolytic media for cellulose nanocrystal production. Biomacromolecules 17:3025–3032. https://doi.org/10.1021/acs.biomac.6b00910 CrossRefPubMed

Smirnov MA, Vorobiov VK, Sokolova MP et al (2018) Electrochemical properties of supercapacitor electrodes based on polypyrrole and enzymatically prepared cellulose nanofibers. Polym Sci Ser C 60:228–239. https://doi.org/10.1134/S1811238218020194 CrossRef

Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082. https://doi.org/10.1021/cr300162p CrossRefPubMed

Sokolova MP, Smirnov MA, Samarov AA et al (2018) Plasticizing of chitosan films with deep eutectic mixture of malonic acid and choline chloride. Carbohydr Polym 197:548–557. https://doi.org/10.1016/j.carbpol.2018.06.037 CrossRefPubMed

Sun H, Li Y, Wu X, Li G (2013) Theoretical study on the structures and properties of mixtures of urea and choline chloride. J Mol Model 19:2433–2441. https://doi.org/10.1007/s00894-013-1791-2 CrossRefPubMed

Suopajärvi T, Sirviö JA, Liimatainen H (2017) Nanofibrillation of deep eutectic solvent-treated paper and board cellulose pulps. Carbohydr Polym 169:167–175. https://doi.org/10.1016/j.carbpol.2017.04.009 CrossRefPubMed

Surov OV, Voronova MI, Afineevskii AV, Zakharov AG (2018a) Polyethylene oxide films reinforced by cellulose nanocrystals: microstructure-properties relationship. Carbohydr Polym 181:489–498. https://doi.org/10.1016/j.carbpol.2017.10.075 CrossRefPubMed

Surov OV, Voronova MI, Rubleva NV et al (2018b) A novel effective approach of nanocrystalline cellulose production: oxidation–hydrolysis strategy. Cellulose 25:5035–5048. https://doi.org/10.1007/s10570-018-1910-4 CrossRef

Tang J, Berry RM, Tam KC (2016) Stimuli-responsive cellulose nanocrystals for surfactant-free oil harvesting. Biomacromolecules 17:1748–1756. https://doi.org/10.1021/acs.biomac.6b00144 CrossRefPubMed

Tenhunen T-M, Lewandowska AE, Orelma H et al (2018) Understanding the interactions of cellulose fibres and deep eutectic solvent of choline chloride and urea. Cellulose 25:137–150. https://doi.org/10.1007/s10570-017-1587-0 CrossRef

Troter DZ, Todorović ZB, Đokić-Stojanović DR et al (2016) Application of ionic liquids and deep eutectic solvents in biodiesel production: a review. Renew Sustain Energy Rev 61:473–500CrossRef

Wang Y, Wang X, Xie Y, Zhang K (2018) Functional nanomaterials through esterification of cellulose: a review of chemistry and application. Cellulose 25:3703–3731. https://doi.org/10.1007/s10570-018-1830-3 CrossRef

Weerasinghe S, Smith PE (2003) A Kirkwood–Buff derived force field for sodium chloride in water. J Phys Chem B 119:3891–3898CrossRef

Wu W, Huang F, Pan S et al (2015) Thermo-responsive and fluorescent cellulose nanocrystals grafted with polymer brushes. J Mater Chem A Mater energy Sustain 3:1995–2005. https://doi.org/10.1039/C4TA04761C CrossRef

Ying Z, Wu D, Wang Z et al (2018) Rheological and mechanical properties of polylactide nanocomposites reinforced with the cellulose nanofibers with various surface treatments. Cellulose 25:3955–3971. https://doi.org/10.1007/s10570-018-1862-8 CrossRef

Zainal-Abidin MH, Hayyan M, Hayyan A, Jayakumar NS (2017) New horizons in the extraction of bioactive compounds using deep eutectic solvents: a review. Anal Chim Acta 979:1–23. https://doi.org/10.1016/j.aca.2017.05.012 CrossRefPubMed

Zhang Q, Vigier KDO, Royer S, Jerome F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev Chem Soc Rev 41:7108–7146. https://doi.org/10.1039/c2cs35178a CrossRefPubMed

Zhou Y, Saito T, Bergström L, Isogai A (2018) Acid-free preparation of cellulose nanocrystals by TEMPO oxidation and subsequent cavitation. Biomacromolecules 19:633–639. https://doi.org/10.1021/acs.biomac.7b01730 CrossRefPubMed

Zhu P, Gu Z, Hong S, Lian H (2017) One-pot production of chitin with high purity from lobster shells using choline chloride–malonic acid deep eutectic solvent. Carbohydr Polym 177:217–223. https://doi.org/10.1016/j.carbpol.2017.09.001 CrossRefPubMed

Titel: Green method for preparation of cellulose nanocrystals using deep eutectic solvent
verfasst von: Michael A. Smirnov
Maria P. Sokolova
Dmitry A. Tolmachev
Vitaly K. Vorobiov
Igor A. Kasatkin
Nikolay N. Smirnov
Anastasya V. Klaving
Natalya V. Bobrova
Natalia V. Lukasheva
Alexander V. Yakimansky
Publikationsdatum: 21.03.2020
Verlag: Springer Netherlands
Erschienen in: Cellulose / Ausgabe 8/2020
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-020-03100-1

Springer Professional

Abstract

Graphic abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Springer Professional "Wirtschaft+Technik"

Weitere Artikel der Ausgabe 8/2020

The efficient removal of anionic and cationic dyes from aqueous media using hydroxyethyl starch-based hydrogels

A bio-resourced mannitol phospholipid ammonium reactive flame retardant for cotton with efficient antiflaming and durability

Incorporating graphene oxide into biomimetic nano-microfibrous cellulose scaffolds for enhanced breast cancer cell behavior

A modified X-model of the oil-impregnated bushing including non-uniform thermal aging of cellulose insulation

Tomato plant residue as new renewable source for cellulose production: extraction of cellulose nanocrystals with different surface functionalities

Needleless electrospun carboxymethyl cellulose/polyethylene oxide mats with medicinal plant extracts for advanced wound care applications