2 chloro 4 4 5 5 tetramethyl 1 3 2 dioxaphospholane

Manufactured by Merck Group

Sourced in Belgium, Germany, United States

2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane is a chemical compound that functions as a source of phosphorus in various organic synthesis reactions. It is a clear, colorless liquid with a distinctive odor. The compound is widely used in the pharmaceutical, agricultural, and materials science industries as a key intermediate in the production of a variety of chemical compounds.

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14 protocols using 2 chloro 4 4 5 5 tetramethyl 1 3 2 dioxaphospholane

Quantitative Phosphorous NMR Analysis

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³¹P-NMR spectroscopic analyses were recorded on a Bruker Instrument AVANCE400 spectrometer (Milano, Italy). Acquisition and data treatment were performed with Bruker TopSpin 3.2 software (Milano, Italy). The spectra were collected at 29 °C with a 4-s acquisition time, 5-s relaxation delay, and 256 scans. Prior to analysis, samples were dried for 24 h under vacuum and then derivatized according to the following procedure.
A lignin sample (40 mg) was completely dissolved in 300 μL of N,N-dimethylformamide. To this solution, the following components were added: 200 μL of dry pyridine, 100 μL of solution of internal standard (10 mg of Endo-N-hydroxy-5-norbornene-2,3-dicarboximide (Sigma 226378) dissolved in 0.5 mL of a mixture of pyridine and CDCl₃ 1.6:1 v/v), 50 μL of solution of relaxation agent (5.7 mg of chromium (III) acetylacetonate (Sigma 574082) dissolved in 0.5 mL of a mixture of pyridine and CDCl₃ 1.6:1 v/v), 100 μL of 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (Sigma 447536), and at the end 200 μL CDCl₃. The solution was centrifuged if necessary. All chemical shifts reported were related to the reaction product of the phosphorylating agent with water, which gave a signal at 132.2 ppm.

Allegretti C., Boumezgane O., Rossato L., Strini A., Troquet J., Turri S., Griffini G, & D’Arrigo P. (2020). Tuning Lignin Characteristics by Fractionation: A Versatile Approach Based on Solvent Extraction and Membrane-Assisted Ultrafiltration. Molecules, 25(12), 2893.

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Characterization of Kraft Lignin from Norway Spruce

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Wood chips were obtained from Norway spruce (Picea abies). Kraft lignin from Norway spruce (Picea abies) was obtained from processed black liquor in the LignoBoost process.
All water used in the experiments was Milli-Q water (Millipore, Q-POD, Millipak 0.22 μm filter). Ethanol (absolute) and Tetrahydrofuran (HPLC grade) were purchased from VWR chemicals. Sulfuric acid (>95%, analytical grade) and acetic anhydride (99.7%, analytical grade) from Fischer chemicals. Pyridine (anhydrous, 99.8%), endo-N-hydroxy-5-norbornene-2,3-dicarboximide (eHNDI; 97%), chromium(iii) acetylacetonate (Cr(acac₃); 99.99%), 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (Cl-TMDP; 95%), [D₆] DMSO (99.9 at% D), N,N-dimethylformamide (anhydrous, 99.8%), CDCl₃ (≥99.8 at% D) were purchased from Sigma–Aldrich. Acetone (VWR chemicals, lot #19F064007); 0.45 μm membrane filters (Fisherbrand, PTFE, 0.45 μm) were used.

Pylypchuk I.V., Karlsson M., Lindén P.A., Lindström M.E., Elder T., Sevastyanova O, & Lawoko M. (2023). Molecular understanding of the morphology and properties of lignin nanoparticles: unravelling the potential for tailored applications. Green Chemistry, 25(11), 4415-4428.

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Kraft Lignin Modification and Functionalization

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Kraft lignin (total hydroxyl group content: 6.13 mmol g^–1 determined by ³¹P NMR spectroscopy^{37 (link)}), methacrylic
anhydride, triethylamine, 2,2′-(ethylenedioxy)bis(ethylamine)—EDBEA,
spermine, spermidine, lithium chloride, 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane, endo-N-hydroxy-5-norbornene-2,3-dicarboximide,
pyridine, deuterated chloroform, and chromium(III)acetylacetonate,
tebuconazole, and boscalid were purchased from Sigma-Aldrich and used
as received. Azoxystrobin and pyraclostrobin were purchased from TRC,
Canada. Dimethylformamide (DMF) and isopropanol were obtained from
Merck. Kraft lignin and lithium chloride were dried overnight at 70
°C in a vacuum oven before use. The anionic surfactant sodium
dodecyl sulfate (SDS) was purchased from Alfa Aesar and used as received.

Machado T.O., Beckers S.J., Fischer J., Müller B., Sayer C., de Araújo P.H., Landfester K, & Wurm F.R. (2020). Bio-Based Lignin Nanocarriers Loaded with Fungicides as a Versatile Platform for Drug Delivery in Plants. Biomacromolecules, 21(7), 2755-2763.

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Depolymerization of Organosolv Lignins

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Dihydroconiferyl alcohol (DCA, 98%), octanoic acid (≥98%), decanoic acid (≥98%), lauric acid (for synthesis), tert-butanol (≥99%), propyl gallate (PG, ≥98%), ethyl acetate (≥99.5%), acetonitrile (≥99.9%), 2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP), N-Hydroxy-5-norbornene-2,3-dicarboxylic acid imide (NHND, 97%), 5% Pd/C and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals were purchased from Sigma-Aldrich. (Hoeilaart, Belgium). Immobilized lipase B from C. antarctica (Novozym^® 435) was a gift from Novozymes (Bagsvaerd, Denmark). Molecular sieves (3 Å, 1.6–2.5 mm, technical, water absorption capacity 0.2 g/g) were acquired at VWR. Hexanoic acid (98%) and silica gel 60 (42–60 µm, 230–400 mesh) were purchased from Merck (Hoeilaart, Belgium). Petroleum ether (b.p = 40–60 °C), butylated hydroxytoluene (BHT, 99.8%) and butylated hydroxyanisole (BHA, 98%) were purchased from Acros Organics (Geel, Belgium).
Technical organosolv lignins were supplied by CIMV (botanical origin: wheat straw) and Fraunhofer (botanical origin: beech wood). These lignins were depolymerized as described in Section 2.6.

Martinez-Garcia M., Gracia-Vitoria J., Vanbroekhoven K., Dejonghe W, & Satyawali Y. (2023). Selective Enzymatic Esterification of Lignin-Derived Phenolics for the Synthesis of Lipophilic Antioxidants. Antioxidants, 12(3), 657.

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Synthesis and Characterization of Organophosphate Compounds

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Maleic anhydride (>99%), 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (95%), chromium acetylacetonate (>97%), N-Hydroxyphtalimide (97%), acetonitrile (HPLC grade), chloroform-d (99.8%), and pyridine (99.8%) were acquired from Sigma-Aldrich (Steinheim, Germany). 1-butyl-3-methylimidazolium hydrogen sulfate [Bmim][HSO₄] (98%) was produced by Solvionic SA (Verniole, France).

Husson E., Hulin L., Hadad C., Boughanmi C., Stevanovic T, & Sarazin C. (2019). Acidic Ionic Liquid as Both Solvent and Catalyst for Fast Chemical Esterification of Industrial Lignins: Performances and Regioselectivity. Frontiers in Chemistry, 7, 578.

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Extraction and Analysis of Bioactive Compounds

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Sodium hydroxide, sodium chloride, aluminum chloride hexahydrate, p-toluensulfonic acid monohydrate (≥98.5), 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (95%), pyridine, chromium(iii)acetylacetonate, oleuropein, tyrosol, levulinic acid, 5-(hydroxymethyl)furfural, 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt, and pyrazine were purchased from Sigma-Aldrich (St. Louis, MO, USA). Hydrochloric acid 37% was provided from Panreac (Barcelona, Spain). Ethyl acetate was obtained from Scharlau (Barcelona, Spain) while maleic acid, CDCl3 (+0.03% vol. TMS), deuterium oxide, and cyclohexanol were purchased from Fluka™ (St. Gallen, Switzerland), VWR Chemicals (Solon, OH, USA), and Acros Organics (Geel, Belgium), respectively.

Huertas-Alonso A.J., Gavahian M., González-Serrano D.J., Hadidi M., Salgado-Ramos M., Sánchez-Verdú M.P., Simirgiotis M.J., Barba F.J., Franco D., Lorenzo J.M, & Moreno A. (2021). Valorization of Wastewater from Table Olives: NMR Identification of Antioxidant Phenolic Fraction and Microwave Single-Phase Reaction of Sugary Fraction. Antioxidants, 10(11), 1652.

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Quantitative Phosphorus Analysis by NMR

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³¹P NMR spectroscopic analyses were recorded on a Bruker Instrument AVANCE400 spectrometer (Milano, Italy). The acquisition and data treatment were performed with Bruker TopSpin 3.2 software (Milano, Italy). The spectra were collected at 29 °C with a 4 s acquisition time, 5 s relaxation delay, and 256 scans. Prior to the analysis, the samples were dried for 24 h under a vacuum and then derivatized according to the following procedure.
The sample (40 mg) was completely dissolved in 300 μL of N,N-dimethylformamide. To this solution, the following components were added: 200 μL of dry pyridine, 100 μL of solution of an internal standard (10 mg of Endo-N-hydroxy-5-norbornene-2,3-dicarboximide (Sigma 226378) dissolved in 0.5 mL of a mixture of pyridine and CDCl₃ 1.6:1 v/v), 50 μL of a relaxation agent solution (5.7 mg of chromium (III) acetylacetonate (Sigma 574082) dissolved in 0.5 mL of a mixture of pyridine and CDCl₃ 1.6:1 v/v), 100 μL of 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (Sigma 447536), and, at the end, 200 μL of CDCl₃. The solution was centrifuged and/or filtered if necessary. All the chemical shifts reported were related to the reaction product of the phosphorylating agent with water, which gave a signal at 132.2 ppm.

Allegretti C., Bellinetto E., D’Arrigo P., Ferro M., Griffini G., Rossato L.A., Ruffini E., Schiavi L., Serra S., Strini A, & Turri S. (2022). Fractionation of Raw and Parboiled Rice Husks with Deep Eutectic Solvents and Characterization of the Extracted Lignins towards a Circular Economy Perspective. Molecules, 27(24), 8879.

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Kraft Lignin Modification Protocols

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The lignin used in this
study was Biopiva 100 kraft lignin (UPM, Finland). Etax A (≥94.0%)
ethanol was purchased from Altia Industrial. AnalaR NORMAPUR (≥99.5%),
tetrahydrofuran (THF), and acetone were purchased from VWR Chemicals
BDH. Technical-grade glycerol diglycidyl ether, dimethylformamide
(99.8%), pyridine (99.8%), N-hydroxy-5-norbornene-2,3-dicarboxylic
acid imine (97.0%), chromium(III) acetylacetonate (≥98.0%),
2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (95%), and chloroform-D
(99.8%) were purchased from Sigma-Aldrich. All chemicals were used
as received.

Henn K.A., Forsman N., Zou T, & Österberg M. (2021). Colloidal Lignin Particles and Epoxies for Bio-Based, Durable, and Multiresistant Nanostructured Coatings. ACS Applied Materials & Interfaces, 13(29), 34793-34806.

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Lignin-based 3D Printing Resin Development

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Softwood
kraft lignin was acquired from an industrial source in the southeastern
USA and was used after purification following a published methodology.^{31 (link)} That is, shortly, the received dry kraft lignin
was first suspended and stirred in the NaOH solution with EDTA-2Na⁺. The stirred mixture was then filtrated through a filter
paper (Whatman 1), and the filtrate was then gradually acidified to
pH = 3.0 with 2 M H₂SO₄ and then stored at −20
°C overnight. After thawing, the precipitates were collected
by centrifugation and washed thoroughly with deionized water. The
obtained air-dried powder was then used in the following 3D printing
procedure. The hydroxyl content on the softwood kraft lignin was characterized
by ³¹P NMR in the Supporting Information (Figure S2 and Table S1).
Photoreactive methacrylate
resins (product code: RS-F2-GPCL-04), including methacrylate monomer
and oligomer and initiator, were purchased from Formlabs, Inc. Acetone
(≥99.5%) and dimethyl sulfoxide (DMSO, ≥99.9%) were
supplied by Sigma-Aldrich Inc. 2-Chloro-4,4,5,5-tetramethyl-1,3,2
dioxaphospholane, endo-N-hydroxy-5-norbornene-2,3-dicarboximide,
pyridine, and deuterated chloroform and chromium acetylacetonate for
NMR were all of analytical grade and purchased from Sigma-Aldrich.
Isopropyl alcohol (≥99.5%) was provided by Fisher Chemical.
All chemicals were used as received.

Zhang S., Li M., Hao N, & Ragauskas A.J. (2019). Stereolithography 3D Printing of Lignin-Reinforced Composites with Enhanced Mechanical Properties. ACS Omega, 4(23), 20197-20204.

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Lignin Modification Protocol

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Dimethyl sulfate (DMS), sodium
hydroxide (NaOH), sulfuric acid (95.0–98.0%), anhydrous m ethanol
(99.8%), anhydrous dioxane (99.8%), p-toluene sulfonic
acid, sodium borohydride (NaBH₄), ethanol (99.9%), acetone
(≥99.5%), hydrochloric acid (HCl), acetic anhydride, 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), and
2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP; all analytical
grades) were purchased from Sigma-Aldrich. 1,1-Diphenyl-2-picrylhydrazyl
stable radical was purchased from Thermo Fisher. Softwood Kraft lignin
(Indulin AT) is a commercially available technical lignin. Prior to
conducting the experiments, Indulin AT (Ind-AT) was dried under a
vacuum overnight with the aid of P₂O₅. Modifications
of the lignin were carried out using reported protocols.^{34 ,37 (link)}

Diment D., Tkachenko O., Schlee P., Kohlhuber N., Potthast A., Budnyak T.M., Rigo D, & Balakshin M. (2023). Study toward a More Reliable Approach to Elucidate the Lignin Structure–Property–Performance Correlation. Biomacromolecules, 25(1), 200-212.

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