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Erschienen in: Cellulose 12/2017

16.10.2017 | Original Paper

Esterification of bagasse cellulose with metal salts as efficient catalyst in mechanical activation-assisted solid phase reaction system

verfasst von: Tao Gan, Yanjuan Zhang, Yang Su, Huayu Hu, Aimin Huang, Zuqiang Huang, Dong Chen, Mei Yang, Juan Wu

Erschienen in: Cellulose | Ausgabe 12/2017

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Abstract

The present study focused on investigating the catalytic mechanism of metal salts (sodium hypophosphite, sodium bisulfate and ammonium ferric sulfate) for esterification of bagasse cellulose carried out by mechanical activation-assisted solid phase reaction in a stirring ball mill. FTIR analysis of the products confirmed that these metal salts could catalyze the esterification of cellulose. XRD, SEM, FTIR, and 31P-NMR analyses of different samples indicated a synergistic effect between metal salt and ball milling, and the presence of metal salts enhanced the destruction on crystal structure of cellulose by mechanical force. The catalytic mechanism of three metal salts was difference: sodium bisulfate and ammonium ferric sulfate belonged to the catalytic mechanism of protonic acid and Lewis acid, respectively, while the catalytic mechanism of sodium hypophosphite was considered as that it could react with maleic acid to form active intermediates under ball milling.

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Literatur
Zurück zum Zitat Abhilash PC, Singh N (2008) Influence of the application of sugarcane bagasse on lindane (γ-HCH) mobility through soil column: implication for biotreatment. Bioresour Technol 99(18):8961–8966PubMedCrossRef Abhilash PC, Singh N (2008) Influence of the application of sugarcane bagasse on lindane (γ-HCH) mobility through soil column: implication for biotreatment. Bioresour Technol 99(18):8961–8966PubMedCrossRef
Zurück zum Zitat Barbosa SL, Dabdoub MJ, Hurtado GR, Klein SI, Baroni ACM, Cunha C (2006) Solvent free esterification reactions using Lewis acids in solid phase catalysis. Appl Catal A-Gen 313(2):146–150CrossRef Barbosa SL, Dabdoub MJ, Hurtado GR, Klein SI, Baroni ACM, Cunha C (2006) Solvent free esterification reactions using Lewis acids in solid phase catalysis. Appl Catal A-Gen 313(2):146–150CrossRef
Zurück zum Zitat Bassan IAL, Nascimento DR, San Gil RAS, Pais Da Silva MI, Moreira CR, Gonzalez WA Jr, Faro AC, Onfroy T, Lachter ER (2013) Esterification of fatty acids with alcohols over niobium phosphate. Fuel Process Technol 106:619–624CrossRef Bassan IAL, Nascimento DR, San Gil RAS, Pais Da Silva MI, Moreira CR, Gonzalez WA Jr, Faro AC, Onfroy T, Lachter ER (2013) Esterification of fatty acids with alcohols over niobium phosphate. Fuel Process Technol 106:619–624CrossRef
Zurück zum Zitat Cao X, Sun S, Peng X, Zhong L, Sun R, Jiang D (2013) Rapid synthesis of cellulose esters by transesterification of cellulose with vinyl esters under the catalysis of NaOH or KOH in DMSO. J Agric Food Chem 61(10):2489–2495PubMedCrossRef Cao X, Sun S, Peng X, Zhong L, Sun R, Jiang D (2013) Rapid synthesis of cellulose esters by transesterification of cellulose with vinyl esters under the catalysis of NaOH or KOH in DMSO. J Agric Food Chem 61(10):2489–2495PubMedCrossRef
Zurück zum Zitat Charmot A, Katz A (2010) Unexpected phosphate salt-catalyzed hydrolysis of glycosidic bonds in model disaccharides: cellobiose and maltose. J Catal 276(1):1–5CrossRef Charmot A, Katz A (2010) Unexpected phosphate salt-catalyzed hydrolysis of glycosidic bonds in model disaccharides: cellobiose and maltose. J Catal 276(1):1–5CrossRef
Zurück zum Zitat Chundawat SPS, Bellesia G, Uppugundla N, Da Costa Sousa L, Gao D, Cheh AM, Agarwal UP, Bianchetti CM, Phillips GN, Langan P, Balan V, Gnanakaran S, Dale BE (2011) Restructuring the crystalline cellulose hydrogen bond network enhances its depolymerization rate. J Am Chem Soc 133(29):11163–11174PubMedCrossRef Chundawat SPS, Bellesia G, Uppugundla N, Da Costa Sousa L, Gao D, Cheh AM, Agarwal UP, Bianchetti CM, Phillips GN, Langan P, Balan V, Gnanakaran S, Dale BE (2011) Restructuring the crystalline cellulose hydrogen bond network enhances its depolymerization rate. J Am Chem Soc 133(29):11163–11174PubMedCrossRef
Zurück zum Zitat Condron LM, Goh KM, Newman RH (1985) Nature and distribution of soil phosphorus as revealed by a sequential extraction method followed by 31P nuclear magnetic resonance analysis. Eur J Soil Sci 36(2):199–207CrossRef Condron LM, Goh KM, Newman RH (1985) Nature and distribution of soil phosphorus as revealed by a sequential extraction method followed by 31P nuclear magnetic resonance analysis. Eur J Soil Sci 36(2):199–207CrossRef
Zurück zum Zitat Cr Py L, Chaveriat L, Banoub J, Martin P, Joly N (2009) Synthesis of cellulose fatty esters as plastics-influence of the degree of substitution and the fatty chain length on mechanical properties. ChemSusChem 2(2):165–170CrossRef Cr Py L, Chaveriat L, Banoub J, Martin P, Joly N (2009) Synthesis of cellulose fatty esters as plastics-influence of the degree of substitution and the fatty chain length on mechanical properties. ChemSusChem 2(2):165–170CrossRef
Zurück zum Zitat Crawford D, Casaban J, Haydon R, Giri N, McNally T, James SL (2015) Synthesis by extrusion: continuous, large-scale preparation of MOFs using little or no solvent. Chem Sci 6(3):1645–1649PubMedPubMedCentralCrossRef Crawford D, Casaban J, Haydon R, Giri N, McNally T, James SL (2015) Synthesis by extrusion: continuous, large-scale preparation of MOFs using little or no solvent. Chem Sci 6(3):1645–1649PubMedPubMedCentralCrossRef
Zurück zum Zitat Da Silva ASA, Inoue H, Endo T, Yano S, Bon EPS (2010) Milling pretreatment of sugarcane bagasse and straw for enzymatic hydrolysis and ethanol fermentation. Bioresour Technol 101(19):7402–7409PubMedCrossRef Da Silva ASA, Inoue H, Endo T, Yano S, Bon EPS (2010) Milling pretreatment of sugarcane bagasse and straw for enzymatic hydrolysis and ethanol fermentation. Bioresour Technol 101(19):7402–7409PubMedCrossRef
Zurück zum Zitat Dankovich TA, Hsieh Y (2007) Surface modification of cellulose with plant triglycerides for hydrophobicity. Cellulose 14(5):469–480CrossRef Dankovich TA, Hsieh Y (2007) Surface modification of cellulose with plant triglycerides for hydrophobicity. Cellulose 14(5):469–480CrossRef
Zurück zum Zitat Fischer S, Leipner H, Thummler K, Brendler E, Peters J (2003) Inorganic molten salts as solvents for cellulose. Cellulose 10(3):227–236CrossRef Fischer S, Leipner H, Thummler K, Brendler E, Peters J (2003) Inorganic molten salts as solvents for cellulose. Cellulose 10(3):227–236CrossRef
Zurück zum Zitat French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21(2):885–896CrossRef French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21(2):885–896CrossRef
Zurück zum Zitat Fumagalli M, Ouhab D, Boisseau SM, Heux L (2013) Versatile gas-phase reactions for surface to bulk esterification of cellulose microfibrils aerogels. Biomacromol 14(9):3246–3255CrossRef Fumagalli M, Ouhab D, Boisseau SM, Heux L (2013) Versatile gas-phase reactions for surface to bulk esterification of cellulose microfibrils aerogels. Biomacromol 14(9):3246–3255CrossRef
Zurück zum Zitat Gillingham EL, Lewis DM, Voncina B (1999) An FTIR study of anhydride formation on heating butane-tetracarboxylic acid in the presence of various catalysts. Text Res J 69(12):949–955CrossRef Gillingham EL, Lewis DM, Voncina B (1999) An FTIR study of anhydride formation on heating butane-tetracarboxylic acid in the presence of various catalysts. Text Res J 69(12):949–955CrossRef
Zurück zum Zitat Granstrom M, Kavakka J, King A, Majoinen J, Makela V, Helaja J, Hietala S, Virtanen T, Maunu S, Argyropoulos DS, Kilpelainen I (2008) Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride. Cellulose 15(3):481–488CrossRef Granstrom M, Kavakka J, King A, Majoinen J, Makela V, Helaja J, Hietala S, Virtanen T, Maunu S, Argyropoulos DS, Kilpelainen I (2008) Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride. Cellulose 15(3):481–488CrossRef
Zurück zum Zitat Granstrom M, Paakko MKN, Jin H, Kolehmainen E, Kilpelainen I, Ikkala O (2011) Highly water repellent aerogels based on cellulose stearoyl esters. Polym Chem 2(8):1789–1796CrossRef Granstrom M, Paakko MKN, Jin H, Kolehmainen E, Kilpelainen I, Ikkala O (2011) Highly water repellent aerogels based on cellulose stearoyl esters. Polym Chem 2(8):1789–1796CrossRef
Zurück zum Zitat Hu H, Li H, Zhang Y, Chen Y, Huang Z, Huang A, Zhu Y, Qin X, Lin B (2015) Green mechanical activation-assisted solid phase synthesis of cellulose esters using a co-reactant: effect of chain length of fatty acids on reaction efficiency and structure properties of products. RSC Adv 5(27):20656–20662CrossRef Hu H, Li H, Zhang Y, Chen Y, Huang Z, Huang A, Zhu Y, Qin X, Lin B (2015) Green mechanical activation-assisted solid phase synthesis of cellulose esters using a co-reactant: effect of chain length of fatty acids on reaction efficiency and structure properties of products. RSC Adv 5(27):20656–20662CrossRef
Zurück zum Zitat Huang K, Wang B, Cao Y, Li H, Wang J, Lin W, Mu C, Liao D (2011) Homogeneous preparation of cellulose acetate propionate (CAP) and cellulose acetate butyrate (CAB) from sugarcane bagasse cellulose in ionic liquid. J Agric Food Chem 59(10):5376–5381CrossRef Huang K, Wang B, Cao Y, Li H, Wang J, Lin W, Mu C, Liao D (2011) Homogeneous preparation of cellulose acetate propionate (CAP) and cellulose acetate butyrate (CAB) from sugarcane bagasse cellulose in ionic liquid. J Agric Food Chem 59(10):5376–5381CrossRef
Zurück zum Zitat Huang Z, Tan Y, Zhang Y, Liu X, Hu H, Qin Y, Huang H (2012a) Direct production of cellulose laurate by mechanical activation-strengthened solid phase synthesis. Bioresour Technol 118:624–627CrossRef Huang Z, Tan Y, Zhang Y, Liu X, Hu H, Qin Y, Huang H (2012a) Direct production of cellulose laurate by mechanical activation-strengthened solid phase synthesis. Bioresour Technol 118:624–627CrossRef
Zurück zum Zitat Huang Z, Wang N, Zhang Y, Hu H, Luo Y (2012b) Effect of mechanical activation pretreatment on the properties of sugarcane bagasse/poly(vinyl chloride) composites. Compos part A-Appl S 43(1):114–120CrossRef Huang Z, Wang N, Zhang Y, Hu H, Luo Y (2012b) Effect of mechanical activation pretreatment on the properties of sugarcane bagasse/poly(vinyl chloride) composites. Compos part A-Appl S 43(1):114–120CrossRef
Zurück zum Zitat James SL, Adams CJ, Bolm C, Braga D, Collier P, Friscic T, Grepioni F, Harris KD, Hyett G, Jones W, Krebs A, Mack J, Maini L, Orpen AG, Parkin IP, Shearouse WC, Steed JW, Waddell DC (2012) Mechanochemistry: opportunities for new and cleaner synthesis. Chem Soc Rev 41(1):413–447PubMedCrossRef James SL, Adams CJ, Bolm C, Braga D, Collier P, Friscic T, Grepioni F, Harris KD, Hyett G, Jones W, Krebs A, Mack J, Maini L, Orpen AG, Parkin IP, Shearouse WC, Steed JW, Waddell DC (2012) Mechanochemistry: opportunities for new and cleaner synthesis. Chem Soc Rev 41(1):413–447PubMedCrossRef
Zurück zum Zitat Jr. Karnitz O, Alves Gurgel LV, Perin De Melo JC, Botaro VR, Sacramento Melo TM, de Freitas Gil RP, Gil LF (2007) Adsorption of heavy metal ion from aqueous single metal solution by chemically modified sugarcane bagasse. Bioresour Technol 98(6):1291–1297CrossRef Jr. Karnitz O, Alves Gurgel LV, Perin De Melo JC, Botaro VR, Sacramento Melo TM, de Freitas Gil RP, Gil LF (2007) Adsorption of heavy metal ion from aqueous single metal solution by chemically modified sugarcane bagasse. Bioresour Technol 98(6):1291–1297CrossRef
Zurück zum Zitat Kim D, Moreno N, Nunes SP (2016) Fabrication of polyacrylonitrile hollow fiber membranes from ionic liquid solutions. Polym Chem 7(1):113–124CrossRef Kim D, Moreno N, Nunes SP (2016) Fabrication of polyacrylonitrile hollow fiber membranes from ionic liquid solutions. Polym Chem 7(1):113–124CrossRef
Zurück zum Zitat Kondo T (1997) The assignment of IR absorption bands due to free hydroxyl groups in cellulose. Cellulose 4(4):281–292CrossRef Kondo T (1997) The assignment of IR absorption bands due to free hydroxyl groups in cellulose. Cellulose 4(4):281–292CrossRef
Zurück zum Zitat Lam E, Luong JHT (2014) Carbon materials as catalyst supports and catalysts in the transformation of biomass to fuels and chemicals. ACS Catal 4(10):3393–3410CrossRef Lam E, Luong JHT (2014) Carbon materials as catalyst supports and catalysts in the transformation of biomass to fuels and chemicals. ACS Catal 4(10):3393–3410CrossRef
Zurück zum Zitat Leng Y, Wang J, Zhu D, Ren X, Ge H, Shen L (2009) Heteropolyanion-based ionic liquids: reaction-induced self-separation catalysts for esterification. Angew Chem Int Edit 48(1):168–171CrossRef Leng Y, Wang J, Zhu D, Ren X, Ge H, Shen L (2009) Heteropolyanion-based ionic liquids: reaction-induced self-separation catalysts for esterification. Angew Chem Int Edit 48(1):168–171CrossRef
Zurück zum Zitat Morales-delaRosa S, Campos-Martin JM, Fierro JLG (2014) Complete chemical hydrolysis of cellulose into fermentable sugars through ionic liquids and antisolvent pretreatments. ChemSusChem 7(12):3467–3475PubMedCrossRef Morales-delaRosa S, Campos-Martin JM, Fierro JLG (2014) Complete chemical hydrolysis of cellulose into fermentable sugars through ionic liquids and antisolvent pretreatments. ChemSusChem 7(12):3467–3475PubMedCrossRef
Zurück zum Zitat Morán JI, Alvarez VA, Cyras VP, Vázquez A (2008) Extraction of cellulose and preparation of nanocellulose from sisal fibers. Cellulose 15(1):149–159CrossRef Morán JI, Alvarez VA, Cyras VP, Vázquez A (2008) Extraction of cellulose and preparation of nanocellulose from sisal fibers. Cellulose 15(1):149–159CrossRef
Zurück zum Zitat Morris CE, Morris NM, TraskMorrell BJ (1996) Interaction of meso-1,2,3,4-butanetetracarboxylic acid with phosphorus-containing catalysts for esterification cross-linking of cellulose. Ind Eng Chem Res 35(3):950–953CrossRef Morris CE, Morris NM, TraskMorrell BJ (1996) Interaction of meso-1,2,3,4-butanetetracarboxylic acid with phosphorus-containing catalysts for esterification cross-linking of cellulose. Ind Eng Chem Res 35(3):950–953CrossRef
Zurück zum Zitat Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124(31):9074–9082PubMedCrossRef Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124(31):9074–9082PubMedCrossRef
Zurück zum Zitat Nishiyama Y, Sugiyama J, Chanzy H, Langan P (2003) Crystal structure and hydrogen bonding system in cellulose Iα from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 125(47):14300–14306PubMedCrossRef Nishiyama Y, Sugiyama J, Chanzy H, Langan P (2003) Crystal structure and hydrogen bonding system in cellulose Iα from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 125(47):14300–14306PubMedCrossRef
Zurück zum Zitat Nowakowski DJ, Woodbridge CR, Jones JM (2008) Phosphorus catalysis in the pyrolysis behaviour of biomass. J Anal Appl Pyrol 83(2):197–204CrossRef Nowakowski DJ, Woodbridge CR, Jones JM (2008) Phosphorus catalysis in the pyrolysis behaviour of biomass. J Anal Appl Pyrol 83(2):197–204CrossRef
Zurück zum Zitat Patyk E, Katrusiak A (2015) Transformable H-bonds and conformation in compressed glucose. Chem Sci 6(3):1991–1995PubMedCrossRef Patyk E, Katrusiak A (2015) Transformable H-bonds and conformation in compressed glucose. Chem Sci 6(3):1991–1995PubMedCrossRef
Zurück zum Zitat Román-Leshkov Y, Davis ME (2011) Activation of carbonyl-containing molecules with solid Lewis acids in aqueous media. ACS Catal 1(11):1566–1580CrossRef Román-Leshkov Y, Davis ME (2011) Activation of carbonyl-containing molecules with solid Lewis acids in aqueous media. ACS Catal 1(11):1566–1580CrossRef
Zurück zum Zitat Rowell RM (1994) Acetyl distribution in acetylated whole wood and reactivity of isolated wood cell-wall components to acetic anhydried. Wood Fiber Sci 26(1):11–18 Rowell RM (1994) Acetyl distribution in acetylated whole wood and reactivity of isolated wood cell-wall components to acetic anhydried. Wood Fiber Sci 26(1):11–18
Zurück zum Zitat Saddawi A, Jones JM, Williams A (2012) Influence of alkali metals on the kinetics of the thermal decomposition of biomass. Fuel Process Technol 104:189–197CrossRef Saddawi A, Jones JM, Williams A (2012) Influence of alkali metals on the kinetics of the thermal decomposition of biomass. Fuel Process Technol 104:189–197CrossRef
Zurück zum Zitat Sehaqui H, Kulasinski K, Pfenninger N, Zimmermann T, Tingaut P (2017) Highly carboxylated cellulose nanofibers via succinic anhydride esterification of wheat fibers and facile mechanical disintegration. Biomacromol 18(1):242–248CrossRef Sehaqui H, Kulasinski K, Pfenninger N, Zimmermann T, Tingaut P (2017) Highly carboxylated cellulose nanofibers via succinic anhydride esterification of wheat fibers and facile mechanical disintegration. Biomacromol 18(1):242–248CrossRef
Zurück zum Zitat Sun RC, Tomkinson J, Wang SQ, Zhu W (2000) Characterization of lignins from wheat straw by alkaline peroxide treatment. Polym Degra. Stabil 67(1):101–109CrossRef Sun RC, Tomkinson J, Wang SQ, Zhu W (2000) Characterization of lignins from wheat straw by alkaline peroxide treatment. Polym Degra. Stabil 67(1):101–109CrossRef
Zurück zum Zitat Uschanov P, Johansson L, Maunu SL, Laine J (2011) Heterogeneous modification of various celluloses with fatty acids. Cellulose 18(2):393–404CrossRef Uschanov P, Johansson L, Maunu SL, Laine J (2011) Heterogeneous modification of various celluloses with fatty acids. Cellulose 18(2):393–404CrossRef
Zurück zum Zitat Zhang W, Liang M, Lu C (2007) Morphological and structural development of hardwood cellulose during mechanochemical pretreatment in solid state through pan-milling. Cellulose 14(5):447–456CrossRef Zhang W, Liang M, Lu C (2007) Morphological and structural development of hardwood cellulose during mechanochemical pretreatment in solid state through pan-milling. Cellulose 14(5):447–456CrossRef
Zurück zum Zitat Zhang Y, Gan T, Luo Y, Zhao X, Hu H, Huang Z, Huang A, Qin X (2014) A green and efficient method for preparing acetylated cassava stillage residue and the production of all-plant fibre composites. Compos Sci Technol 102:139–144CrossRef Zhang Y, Gan T, Luo Y, Zhao X, Hu H, Huang Z, Huang A, Qin X (2014) A green and efficient method for preparing acetylated cassava stillage residue and the production of all-plant fibre composites. Compos Sci Technol 102:139–144CrossRef
Metadaten
Titel
Esterification of bagasse cellulose with metal salts as efficient catalyst in mechanical activation-assisted solid phase reaction system
verfasst von
Tao Gan
Yanjuan Zhang
Yang Su
Huayu Hu
Aimin Huang
Zuqiang Huang
Dong Chen
Mei Yang
Juan Wu
Publikationsdatum
16.10.2017
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 12/2017
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-017-1524-2

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