Trioxane

Manufactured by Merck Group

Sourced in Germany

Trioxane is a colorless, crystalline compound used as a chemical reagent and in the production of other chemical compounds. It is a cyclic trimer of formaldehyde with the chemical formula (CH2O)3. Trioxane is primarily utilized as an intermediate in various chemical synthesis processes.

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1,3,5-trioxane (12 citations)

5 protocols using trioxane

Pulping and Lignin Analysis Protocol

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Pulping: GVL (≥99 wt%), sulfuric acid (95–97.0 wt%), NaBH₄, MgSO₄*7H₂O, NaHSO₃, di(trimethylolpropane) (97%), diphenyl carbonate (99%), Xylose (≥99 wt%), activated charcoal (100 mesh particle size) were purchased from Sigma Aldrich. Ethanol (≥99.5 wt%) was purchased from Anora. Betula Pendula (Silver birch) wood chips were supplied by Stora Enso (Finland). The wood chips were screened according to the SCAN-CM 40:01 (7 and 13 mm) and stored at −20 °C. NaOH pellets (99.2%), H₂O₂ (30%), and Na₂CO₃ (99.8%) were purchased from VWR. Ionic liquid (1,5-diazabicyclo[4.3.0]non-5-enium acetate) was synthesized by the combination of acetic acid (glacial, 100% for analysis; Merck, Germany) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN; Fluorochem Ltd.)in a reactor at 70 °C [28 ,29 ].
Afilan CVS and Leomin PN for spin finish were purchased from Archroma. Priamine™ 1074 for polyhydroxyurethane production was purchased from Croda GmbH. Pure sodium silicate for fabric bleaching was purchased from Merck.
Lignin NMR: Deuterated chloroform (CDCl₃), pyridine, deuterated dimethyl sulfoxide (DMSO‑d₆), endo-n-hydroxy-5-norbornene-2,3-dicarboximide (e-HNDI), chromium (III) acetylacetonate (Cr(acac)₃), 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP) and trioxane were purchased from Sigma-Aldrich.

Granatier M., Lê H.Q., Ma Y., Rissanen M., Schlapp-Hackl I., Diment D., Zaykovskaya A., Pokki J.P., Balakshin M., Louhi-Kultanen M., Alopaeus V, & Sixta H. (2023). Gamma-valerolactone biorefinery: Catalyzed birch fractionation and valorization of pulping streams with solvent recovery. Heliyon, 9(6), e17423.

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Synthesis and Characterization of BMAT-Terminated pNIPAm

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2,2′-Azobis(2-methylpropionitrile)
(AIBN, 98%), N-isopropylacrylamide (NIPAm,
97%), tert-butyl acrylate (tBuAc,
contains 10–20 ppm monomethyl ether hydroquinone as inhibitor,
98%), trioxane (⩾99.9%), trifluoroacetic acid (TFA, ⩾99%),
concentrated HCl (37% solution in water), and dioxane (anhydrous,
99.8%) were obtained from Sigma-Aldrich, Germany, and used without
further purification unless noted otherwise. NIPAm was recrystallized
twice from a mixture of hexane and acetone. tBuAc
was passed over a short column of Al₂O₃ to remove
the inhibitor. AIBN was recrystallized thrice from MeOH. Bis(2-methylpropionic
acid)trithiocarbonate^{20 (link),21 (link)} (BMAT) and BMAT-terminated pNIPAm^{21 (link)} were synthesized as described in the literature,
with NMR and SEC characterization described in Table S1. Hexafluoroisopropanol (HFIP, AR), dichloromethane
(DCM, AR), tetrahydrofuran (THF, HPLC-grade), and methanol (MeOH,
HPLC) were obtained from Biosolve, France.

Filippov A.D., van Hees I.A., Fokkink R., Voets I.K, & Kamperman M. (2018). Rapid and Quantitative De-tert-butylation for Poly(acrylic acid) Block Copolymers and Influence on Relaxation of Thermoassociated Transient Networks. Macromolecules, 51(20), 8316-8323.

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Synthesis and Purification of Polymeric Reagents

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Azobisisobutyronitrile
(AIBN, Sigma-Aldrich) was recrystallized from methanol prior to use.
Isobornyl acrylate (IBA; technical, Sigma-Aldrich) and lauryl acrylate
(LA; >98%, TCI) were passed over a basic alumina column prior to
use
to remove the stabilizer. Methyl acrylate (MA; 99%, Sigma-Aldrich)
was distilled prior to use. Pyridine, dichloromethane (DCM), and triethylamine
were distilled over calcium hydride (CaH₂) prior to use.
Cyanomethyl dodecyl trithiocarbonate (CDT) was synthesized according
to a procedure mentioned in the literature.^{44 (link)} 2-(Dodecylthiocarbonothioylthio)-2-methylpropionic acid (DDMAT;
98%, Sigma-Aldrich), trioxane (≥99%, Sigma-Aldrich), biphenyl
(>99%, Sigma-Aldrich), acetophenone (AP; 99%, Sigma-Aldrich), sodium
sulfate (≥99%, Sigma-Aldrich), acetic anhydride (≥99%,
Sigma-Aldrich), trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]-malononitrile (DCTB; Sigma-Aldrich,
>98%), potassium trifluoroacetate (KTFA; Sigma-Aldrich, 98%), acryloyl
chloride (96%, Alfa Aesar), furfuryl alcohol (≥98%, Fischer
Scientific), hydrogen chloride (HCl; 37% solution in H₂O, Acros Organics), sodium bicarbonate (>99%, Acros organics),
sodium
chloride (≥99.8%, Roth), tert-butyl methylether
(TBME; 99.9%), acetic acid (AcOH; 99.7%), and CDCl₃ (99.8%,
Cambridge Isotope Laboratories) were used as received. All other solvents
were obtained from Biosolve and were used as received.

Stouten J., Vanpoucke D.E., Van Assche G, & Bernaerts K.V. (2020). UV-Curable Biobased Polyacrylates Based on a Multifunctional Monomer Derived from Furfural. Macromolecules, 53(4), 1388-1404.

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Synthesis and Characterization of Polyoxyethylene Diols

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Chemicals: chloroform-d¹, 99.6% (Deutero GmbH, Kastellaun, Germany); dichlorobenzene, anhydrous, 99% (Sigma-Aldrich Chemie GmbH, Taufkirchen, Germany), secure seal, withdrawn under counter current argon flow; dichloromethane, anhydrous, ≥99.8% (Sigma-Aldrich), secure seal, withdrawn under counter current argon flow; dioxolane, anhydrous, 99.8% (Sigma-Aldrich), secure seal, withdrawn under counter current argon flow; n-pentane, technical, >98% (Haltermann Carless, Hamburg, Germany); sulfur trioxide DMF complex, 97+ % (ACROS Organics, Geel, Belgium); triethylamine, >98% (Fluka Analytical, Merck KGaA, Darmstadt, Germany); trioxane, ≥99% (Sigma-Aldrich). These were used as supplied if not stated otherwise. Polyoxyethylene diols A, B, and C were obtained with nominal weights of 1000, 400 and 200 g/mol, respectively, as PEG 1000, (Fluka, Honeywell Specialty Chemicals Seelze GmbH, Seelze, Germany), PEG 400, (Fluka), and PEG 200 for synthesis (Merck KGaA, Darmstadt, Germany); they were then dried in an oil pump vacuum prior to used. The number average molecular weights were determined with gel permeation chromatography, being 1076, 364 and 136 g/mol, respectively.

Hoffmann M., Hermesmann M., Leven M., Leitner W, & Müller T.E. (2022). Semi-Crystalline Polyoxymethylene-co-Polyoxyalkylene Multi-Block Telechels as Building Blocks for Polyurethane Applications. Polymers, 14(5), 882.

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Purification of Monomers for Polymerization

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The monomers ε-caprolactone (ε-CL), ε-decalactone (ε-DL) and ethylene brassylate (EB) (Sigma-Aldrich) were purified via a distillation system which included Na⁰ as a drier reagent, a vacuum pressure at 15 mm Hg and a temperature of 160 °C to achieve complete removal of humidity and oxygen. L-Lactide (L-LA) (Sigma-Aldrich, St. Louis, MO, USA), was purified through a crystallization process into ethyl acetate (J. T. Baker, Radnor, PA, USA) solution (33.33% weight). Other reagents such as TBD (TCI chemicals, Portland, OR, USA), benzyl alcohol and trioxane (Sigma-Aldrich, St. Louis, MO, USA) were used as received. Toluene and methanol were provided by J. T. Baker. Toluene was washed with H₂SO₄, dried in CaCl₂, stirred under reflux conditions with LiAlH₄ and distilled using a sodium/benzophenone complex, while methanol was used as received.

Robles-González F., Rodríguez-Hernández T., Ledezma-Pérez A.S., Díaz de León R., De Jesús-Téllez M.A, & López-González H.R. (2022). Development of Biodegradable Polyesters: Study of Variations in Their Morphological and Thermal Properties through Changes in Composition of Alkyl-Substituted (ε-DL) and Non-Substituted (ε-CL, EB, L-LA) Monomers. Polymers, 14(20), 4278.

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