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28.05.2021 | Communication

N-Methylmorpholine-N-oxide (NMMO): hazards in practice and pitfalls in theory

verfasst von: Thomas Rosenau, Alfred D. French

Erschienen in: Cellulose | Ausgabe 10/2021

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Abstract

The hazards of handling N-methylmorpholine-N-oxide (NMMO) cannot be described often enough, although it is a rather common (co-)solvent for cellulose. Inaccuracies in the literature regarding the chemistry of NMMO, such as its role in solvent systems and in redox systems involving transition metal ions, increase the risk of dangerous failure of the intended reactions which might result in uncontrolled exothermicities, damage of laboratory equipment or even accidents and work safety issues. Therefore, suitable cautionary and mitigation strategy statements regarding the hazards of handling NMMO are encouraged for future publications regarding NMMO and cellulose.

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Adorjan I, Potthast A, Rosenau T, Sixta H, Kosma P (2005) Discoloration of cellulose solutions in N-methylmorpholine-N-oxide (Lyocell) Part 1: studies on model compounds and pulps. Cellulose 12(1):51–57CrossRef

Albini A. (1993) Synthetic utility of amine N-oxides. Synthesis 263–277.

Aslanzadeh S, Berg A, Taherzadeh MJ, Sárvári Horváth I (2014) Biogas production from N-Methylmorpholine-N-oxide (NMMO) pretreated forest residues. Appl Biochem Biotechnol 172(6):2998–3008PubMedCrossRef

Böhmdorfer S, Hosoya T, Röder T, Potthast A, Rosenau T (2017) A cautionary note on thermal runaway reactions in mixtures of 1-alkyl-3-methylimidazolium ionic liquids and N-methylmorpholine-N-oxide. Cellulose 24(5):1927–1932CrossRef

Brodeur G, Telotte J, Stickel JJ, Ramakrishnan S (2016) Two-stage dilute-acid and organic-solvent lignocellulosic pretreatment for enhanced bioprocessing. Biores Technol 220:621–628CrossRef

Cai LY, Ma YL, Ma XX, Lv JM (2016) Improvement of enzymatic hydrolysis and ethanol production from corn stalk by alkali and N-methylmorpholine-N-oxide pretreatments. Biores Technol 212:42–46CrossRef

Coleman KS, Bedel LJL, Osborn JA (2000) Catalytic oxidation of alcohols to aldehydes or ketones using osmium-oxo complexes with sulfoxides or N-methylmorpholine-N-oxide as the co-oxidant: a comparative study. Comptes Rendus Acad Sci - Ser IIc: Chemistry 3(10):765–769

Cope AC, Foster TT, Towle PH (1949) Thermal decomposition of amine oxides to olefins and dialkylhydroxylamines. J Am Chem Soc 71:3929–3935CrossRef

Cuissinat C, Navard P (2006) Swelling and dissolution of cellulose part 1: free floating cotton and wood fibres in N-methylmorpholine-N-oxide–water mixtures. Macromol Symp 244:1–18CrossRef

Dasgupta B, Donaldson WA (1998) Chemoselective, metal-mediated oxidation of (dienol)iron complexes with N-methylmorpholine N-oxide. Tetrahedron Lett 39:343–346CrossRef

Erdman A, Kulpinski P, Grzyb T, Lis S (2016) Preparation of multicolor luminescent cellulose fibers containing lanthanide doped inorganic nanomaterials. J Luminescence 169:520–527CrossRef

Fink HP, Weigel P, Purz HJ, Ganster J (2001) Structure formation of regenerated cellulose materials from NMMO-solutions. Progr Polym Sci 26(9):1473–1524CrossRef

Firgo H, Eibl M, Eichinger D (1995) Lyocell—an ecological alternative. Lenzinger Ber 75:47–50

Gomes M Jr, Antunes OAC (2001) Upjohn catalytic osmium tetroxide oxidation process: Diastereoselective dihydroxylation of monoterpenes. Cat Comm 2(6–7):225–227CrossRef

Goshadrou A, Karimi K, Taherzadeh MJ (2013) Biomass Bioenergy 2013, 49, 95–101. Ethanol and biogas production from birch by NMMO-pretreatment.

Gränacher C, Sallmann R (1939). US Patent 2,179,181.

Hatakeyama M, Ryuno D, Yokota S, Ichinose H, Kitaoka T (2019) One-step synthesis of cellooligomer-conjugated gold nanoparticles in a water-in-oil emulsion system and their application in biological sensing. Coll Surf B Biointerfaces 178:74–79CrossRef

Jusner P, Aoki M, Potthast A, Rosenau T (2020) A cautionary note on “exothermic events” upon contact of carbodiimide coupling agents and the cellulose solvent N-methylmorpholine-N-oxide. Cellulose 27(13):7349–7359CrossRef

Jusner P, Bacher M, Hettegger H, Lê HQ, Potthast A, Sixta H, Rosenau T (2021) On the chemical interactions of the biomass processing agents gamma-valerolactone (GVL) and N-methylmorpholine-N-oxide (NMMO). Green Chem 2021, submitted.

Kitaoka T, Yokota S, Opietnik M, Rosenau T (2011) Synthesis and bio-applications of carbohydrate-gold nanoconjugates with nanoparticle and nanolayer forms. Mat Sci Engineer C 31(6):1221–1229CrossRef

Khodaverdi M, Jeihanipour A, Karimi K, Taherzadeh M (2012) Kinetic modeling of rapid enzymatic hydrolysis of crystalline cellulose after pretreatment by NMMO. J Ind Microbiol Biotechnol 39:429–438PubMedCrossRef

Kulpinski P, Namyslak M, Grzyb T, Lis S (2012) Luminescent cellulose fibers activated by Eu 3+-doped nanoparticles. Cellulose 19(4):1271–1278CrossRef

Kulpinski P, Erdman A, Grzyb T, Lis S (2016) Luminescent cellulose fibers modified with cerium fluoride doped with terbium particles. Polym Compos 37(1):153–160CrossRef

Kuo CH, Lee CK (2009a) Enhancement of enzymatic saccharification of cellulose by cellulose dissolution pretreatments. Carbohydr Polym 77:41–46CrossRef

Kuo CH, Lee CK (2009b) Enhanced enzymatic hydrolysis of sugarcane bagasse by N-methylmorpholine-N-oxide pretreatment. Biores Technol 100: 866–871CrossRef

Lennartsson PR, Niklasson C, Taherzadeh MJ (2011) A pilot study on lignocelluloses to ethanol and fish feed using NMMO pretreatment and cultivation with Zygomycetes in an airlift reactor. Biores Technol 102(6):4425–4432CrossRef

Linton EP (1940) The dipole moment of amine oxides. J Am Chem Soc 62:1945–1948CrossRef

Liu Y, Zhong Q, Wang S, Cai Z (2011) Correlating physical changes and enhanced enzymatic saccharification of pine flour pretreated by N-methylmorpholine-N-oxide. Biomacromol 12(7):2626–2632CrossRef

Manian AP, Ruef H, Bechtold T (2007) Spun-dyed Lyocell. Dyes Pigment 74(3):519–524CrossRef

Marini I, Brauneis F (1996) Lyocell - die wichtigsten Unterschiede zu den anderen cellulosischen Fasern. Textilveredlung 31:182–187

Meister G, Wechsler M (1998) Biodegradation of N-Methylmorpholine-N-oxide. Biodegradation 9:91–102PubMedCrossRef

Öztürk HB, Potthast A, Rosenau T, Abu-Rous M, MacNaughtan B, Schuster KC, Mitchell J, Bechtold T (2009) Changes in the intra- and interfibrillar structure of lyocell (Tencel®) fibers caused by NaOH treatment. Cellulose 16(1):37–52CrossRef

Pieterse T (2013) Synlett 24(16):2175–2176. N-Methylmorpholine N-oxide.

Poornejad N, Karimi K, Behzad T (2013) Improvement of saccharification and ethanol production from rice straw by NMMO and [BMIM][OAc] pretreatments. Ind Crops Prod 41:408–413CrossRef

Potthast A, Rosenau T, Kosma P, Chen CL, Gratzl JS (2000) Confirmation of the presence of formaldehyde and N-(Methylene)morpholinium cations as reactive species in the cellulose / NMMO / water system by trapping reactions. Holzforschung 54:101–103CrossRef

Purwandari FA, Sanjaya AP, Millati R, Cahyanto MN, Horváth IS, Niklasson C, Taherzadeh MJ (2013) Pretreatment of oil palm empty fruit bunch (OPEFB) by N-methylmorpholine-N-oxide (NMMO) for biogas production: structural changes and digestion improvement. Biores Technol 128:461–466CrossRef

Rac-Rumijowska O, Fiedot M, Karbownik I, Suchorska-Woźniak P, Teterycz H (2017) Synthesis of silver nanoparticles in NMMO and their in situ doping into cellulose fibers. Cellulose 24(3):1355–1370CrossRef

Rac-Rumijowska O, Maliszewska I, Fiedot-Toboła M, Karbownik I, Teterycz H (2019) Multifunctional nanocomposite cellulose fibers doped in situ with silver nanoparticles. Polymers 11(3):562PubMedCentralCrossRef

Ramakrishnan S, Collier J, Oyetunji R, Stutts B, Burnett R (2010) Enzymatic hydrolysis of cellulose dissolved in N-methyl morpholine oxide/water solutions. Biores Technol 101(13):4965–4970CrossRef

Righi S, Morfino A, Galletti P, Samorì C, Tugnoli A, Stramigioli C (2011) Comparative cradle-to-gate life cycle assessments of cellulose dissolution with 1-butyl-3-methylimidazolium chloride and N-methyl-morpholine-N-oxide. Green Chem 13(2):367–375CrossRef

Rosenau T, Potthast A, Kosma P, Chen CL, Gratzl JS (1999) Autocatalytic decomposition of N-Methylmorpholine-N-oxide induced by mannich intermediates. J Org Chem 64:2166–2167CrossRef

Rosenau T, Potthast A, Sixta H, Kosma P (2001) The chemistry of side reactions and byproduct formation in the system NMMO / cellulose (lyocell process). Progr Polym Sci 26(9):1763–1837CrossRef

Rosenau T, Potthast A, Adorjan I, Hofinger A, Sixta H, Firgo H, Kosma P (2002) Cellulose solutions in N-methylmorpholine-N-oxide (NMMO)—Degradation processes and stabilizers. Cellulose 9(3–4):283–291CrossRef

Rosenau T, Hofinger A, Potthast A, Kosma P (2004) A general, selective high-yield N-demethylation procedure for tertiary amines by solid reagents in a convenient column chromatography-like setup. Org Lett 6(4):541–544PubMedCrossRef

Rosenau T, Potthast A, Milacher W, Adorjan I, Hofinger A, Kosma P (2005a) Discoloration of cellulose solutions in N-methyl-morpholine-N-oxide (Lyocell). Part 2: Isolation and Identification of Chromophores. Cellulose 12(2):197–208.

Rosenau T, Schmid P, Potthast A, Kosma P (2005) Stabilization of cellulose solutions in N-methylmorpholine-N-oxide (Lyocell dopes) by addition of an N-oxide as sacrificial substrate. Holzforschung 59(5):503–506CrossRef

Satari B, Karimi K, Kumar R (2019) Cellulose solvent-based pretreatment for enhanced second-generation biofuel production: a review. Sust Energy Fuels 3(1):11–62CrossRef

Sayyed AJ, Deshmukh NA, Pinjari DV (2019) A critical review of manufacturing processes used in regenerated cellulosic fibres: viscose, cellulose acetate, cuprammonium, LiCl/DMAc, ionic liquids, and NMMO based Lyocell. Cellulose 26(5):2913–2940CrossRef

Shafiei M, Karimi K, Taherzadeh MJ (2010) Pretreatment of spruce and oak by N-methylmorpholine-N-oxide (NMMO) for efficient conversion of their cellulose to ethanol. Biores Technol 101(13):4914–4918CrossRef

Shafiei M, Karimi K, Zilouei H, Taherzadeh MJ (2014) Enhanced ethanol and biogas production from pinewood by NMMO pretreatment and detailed biomass analysis. Bio Med Res Int 469378.

Shah N, Ul-Islam M, Khattak WA, Park JK (2013) Overview of bacterial cellulose composites: a multipurpose advanced material. Carbohydr Polym 98(2):1585–1598PubMedCrossRef

Skwierczyńska M, Runowski M, Kulpiński P, Lis S (2019) Modification of cellulose fibers with inorganic luminescent nanoparticles based on lanthanide(III) ions. Carbohydr Polym 206:742–748PubMedCrossRef

Smiechowicz E, Kulpinski P, Niekraszewicz B, Bacciarelli A (2011) Cellulose fibers modified with silver nanoparticles. Cellulose 18(4):975–985CrossRef

Smiechowicz E, Niekraszewicz B, Kulpinski P, Dzitko K (2018) Antibacterial composite cellulose fibers modified with silver nanoparticles and nanosilica. Cellulose 25(6):3499–3517CrossRef

Smiechowicz E, Niekraszewicz B, Strzelinska M, Zielecka M (2020) Antibacterial fibers containing nanosilica with immobilized silver nanoparticles. Autex Res J 20(4):441–448CrossRef

Stockinger H, Kut OM, Heinzle E (1996) Ozonation of wastewater containing N-methylmorpholine-N-oxide. Water Res 30(8):1745–1748CrossRef

Taherzadeh MJ, Karimi K (2008) Pretreatment of lignocellulosic wastes to improve ethanol and biogas production: a review. Int J Mol Sci 9(9):1621–1651PubMedPubMedCentralCrossRef

Teghammar A, Karimi K, Horváth IS, Taherzadeh MJ (2012) Enhanced biogas production from rice straw, triticale straw and softwood spruce by NMMO pretreatment. Biomass Bioenergy 36:116–120CrossRef

Wikandari R, Millati R, Taherzadeh MJ (2016) Pretreatment of Lignocelluloses With Solvent N-Methylmorpholine N-oxide. In: Biomass Fractionation Technologies for a Lignocellulosic Feedstock Based Biorefinery. Elsevier, 2016. ISBN: 978–012802561–1; 978–012802323–5

Yokota S, Kitaoka T, Opietnik M, Rosenau T, Wariishi H (2008) Synthesis of gold nanoparticles for in situ conjugation with structural carbohydrates. Angew Chem Int Ed Engl 47:9866–9869PubMedCrossRef

Zhang S, Chen C, Duan C, Hu H, Li H, Li J, Liu Y, Ma X, Stavik J, Ni Y (2018) Regenerated cellulose by the lyocell process, a brief review of the process and properties. BioRes 13(2):1–16CrossRef

Titel: N-Methylmorpholine-N-oxide (NMMO): hazards in practice and pitfalls in theory
verfasst von: Thomas Rosenau
Alfred D. French
Publikationsdatum: 28.05.2021
Verlag: Springer Netherlands
Erschienen in: Cellulose / Ausgabe 10/2021
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-021-03860-4

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