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CAS No. : | 87-73-0 | MDL No. : | MFCD09752094 |
Formula : | C6H10O8 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DSLZVSRJTYRBFB-LLEIAEIESA-N |
M.W : | 210.14 | Pubchem ID : | 33037 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 6.0 |
Molar Refractivity : | 39.15 |
TPSA : | 155.52 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -9.36 cm/s |
Log Po/w (iLOGP) : | -0.55 |
Log Po/w (XLOGP3) : | -2.51 |
Log Po/w (WLOGP) : | -3.4 |
Log Po/w (MLOGP) : | -2.98 |
Log Po/w (SILICOS-IT) : | -2.61 |
Consensus Log Po/w : | -2.41 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.11 |
Log S (ESOL) : | 0.77 |
Solubility : | 1230.0 mg/ml ; 5.87 mol/l |
Class : | Highly soluble |
Log S (Ali) : | -0.21 |
Solubility : | 129.0 mg/ml ; 0.613 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 3.47 |
Solubility : | 622000.0 mg/ml ; 2960.0 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.29 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
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bei der Destillation; |
Yield | Reaction Conditions | Operation in experiment |
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74% | With 5 % platinum on carbon; oxygen In water at 80℃; for 10h; | |
21% | With oxygen In water at 110℃; for 2h; | 14 EXAMPLE 14 Testing of gold - platinum on tungsten containing crushed carbon black extrudates in a batch reactor for the oxidation of glucose to glucaric acid EXAMPLE 14 Testing of gold - platinum on tungsten containing crushed carbon black extrudates in a batch reactor for the oxidation of glucose to glucaric acid [0242] Six catalysts were tested for glucose (ADM) oxidation using the following catalyst testing protocol. Catalyst (ca. 16 mg) were weighed into glass vial inserts followed by addition of an aqueous glucose solution (250 μ of 20 wt. %). The glass vial inserts were loaded into a reactor and the reactor was closed. The atmosphere in the reactor was replaced with oxygen and pressurized to 150 psig at room temperature. Reactor was heated to 110°C and maintained at 110°C for 2 hours while vials were shaken. After 2 hours, shaking was stopped and reactor was cooled to 40°C. Pressure in the reactor was then slowly released. The glass vial inserts were removed from the reactor. The solutions were diluted with water and analyzed by ion chromatography with CAD / connectivity detection. A summary of the results is provided in Table 4. |
With nitric acid |
With bromine | ||
With ammonia; water; nitric acid | ||
With dinitrogen tetraoxide; potassium carbonate | ||
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water at 5℃; Electrolysis; | ||
With nitric acid In water at 25℃; | 4.6. Oxidation of d-glucose, 3:1 molar ratio of nitric acid to d-glucose The oxidation process was patterned after the 4:1 molar ratio of nitric acid to d-glucose oxidation process but doubled the ingredient amounts and employed fewer stages. The oxidation procedure was divided into six separate stages in the Recipe Menu of the Labmax Camille software. Stage 1: the temperature was set for 25 °C (and held constant throughout all remaining stages) and the stirring rod speed set at 200 rpm (and held constant throughout all remaining stages), time was set for 1 min. Stage 2: the pressure was set at 0.25 bar above atmospheric (and held constant throughout all remaining stages), and the time was set for 3 min. Stage 3: 86.6 g of 62.3% d-glucose solution was set to be added over 30 min. Stage 4: 10 min hold. Stage 5: 345.8 g of d-glucose solution was set to be added over 90 min. Stage 6: 20 min hold. Once the software was programed, aqueous nitric acid (282 mL, 4.5 mol) was added to the reactor, the reaction recipe was initiated, and the reactor was closed to the atmosphere. | |
With oxygen; nitric acid; sodium nitrite In water at 25 - 30℃; for 3h; | 10 Oxidation procedure 1 (4:1 M ratio of nitric acid to Dmannoseat 25 °C) The oxidation was carried out using the Labmax reactor. Reactionparameters for the oxidation were programed in a series ofstages: Stage 1: The reactor temperature was set at 25 C, the stirringrod speed was set at 200 rpm and maintained throughout theremaining stages. Concentrated nitric acid (70%, 3.00 mol, 187 mL)was added to the reaction vessel, the vessel was closed to theatmosphere, and time set for 1 min. Stage 2: Oxygen was addedto bring the pressure to 0.25 bar and pressure maintained untilthe end of stage 6. Stage 3: D-Mannose [43.3 g of an aqueous62.5% solution containing sodium nitrite (8.7 mmol, 0.6 g)] wasadded over 30 min. Stage 4: A stabilization period with no changein reaction conditions was employed (10 min). Stage 5: D-Mannose[173.9 g of an aqueous 62.2% solution containing sodium nitrite(8.7 mmol, 0.6 g)] was added over 90 min. Stage 6: A second stabilizationperiod (5 min) was employed. Stage 7: The reactor temperaturewas set to 30 C and pressure to 0.5 bar over 1 h. Stage 8.Reaction conditions were maintained over 6 h. Stage 9: The reactionmixture was cooled to 25 C over 10 min and the vesselopened to the atmosphere. | |
With oxygen; nitric acid; sodium nitrite In water at 25℃; for 7h; Autoclave; | 2 “Static Oxidation” A 62.5% (wt/wt) D-glucose solution was prepared by adding solid anhydrous D-glucose to deionized water in a screw-capped flask containing a stir bar. Next, the solution was heated to 65° C. with stirring. Once the glucose was adequately dissolved, the solution was cooled to 40° C. 411 g (4.5 moles) of concentrated nitric acid was then added to the reactor and the iControl software was used to maintain a reaction temperature of 25° C. and an agitation speed of 200 RPM for the duration of the reaction Immediately after the nitric acid was added 0.31 g (4.5 millimoles) of sodium nitrite was added to the reactor and the reactor was sealed and pressurized with 1 barg oxygen. The 62.5% D-glucose solution was dosed into the reactor at a rate of 2.88 g/min until 432.4 g (1.5 moles) had been added (150 min). After a short induction period, the mixture began to react exothermically as indicated by the jacket temperature having to run at colder and colder temperatures to maintain the material temperature of 25° C. After 25 minutes, the jacket was running at 12° C. and brown NOx gasses began to fill the headspace of the reactor and the liquid contents of the reactor turned emerald green in color. After 35 minutes, the jacket temperature was running at 4.5° C. to maintain a reaction temperature of 25° C. The headspace filledwith dark brown NOx gas and the liquid mixture turned dark green. At this time, the reaction began to slowly subside taking about 6 hours for the jacket temperature to rise to 20° C. to maintain a reaction temperature of 25° C. The headspace continued to be filled with dark brown gasses and the liquid mixture continued to be dark green in color until the reaction was fully quenched/terminated by adding a liter of cold water to the reactor. The exothermicity, gas production, and green liquid color observations were shown to be typical of all nitric acid oxidations performed in a closed vessel under oxygen pressure regardless of molar ratio or batch size. | |
With platinum on activated charcoal; oxygen; potassium hydroxide In water at 50℃; for 4h; | 2 Embodiment 2 Depending on the ratio shown in Table 1, as a startingmaterial, glucose is inputted into the reactor at 0.1 g/cc con-centration to aqueous solvent, and then potassium hydroxideis inputted at 1:4 mol ratio to glucose. Then, a platinumcatalyst supported on activated carbon was added to the 50weight % extent to the glucose. Then, the temperature of thereactor is maintained to 50° C., and it was reacted during 4hours while inputting oxygen gas into the reactor and maintaining the pressure at a 1.5 bar level.At the end of the reaction, it was confirmed that glucaricacid was synthesized by performing nuclear magnetic resonance analysis (Bruker AVIII400 Instrument) and FT IRinstrument analysis (Agilent Technologies Cary 600), afterseparating water from reactant (see FIG. 2 and FIG. 3) (‘H at400 MHz, ‘3C at 100 MHz).‘H NMR ö 4.14 (d, J=3.2, 1H),4.09 (d, J=4.4, 1H),3.96 (dd, J=3.2, 2.0, 1H),3.80 (apparently t, J=5.0).‘3C NMR ö 177.1, 176.9, 73.4, 72.6, 72.4, 71.5FT-IR (equipped withATR accessory) 3252, 1742 cm’ | |
With oxygen; sodium hydroxide In water at 60℃; for 3h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid in mehreren Stufen; | ||
bei der Einw. von Aspergillus niger; | ||
bei der Einw. der Nektarhefen Anthomyces Reukaufii oder Amphiernia rubra; |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid | ||
Bildung aus subcutan injizierte d-Gluconsaeure im Organismus des Kaninchens. (Schott konnte diese Bildung nicht bestaetigen); | ||
With UDP-glucose dehydrogenase Enzymatic reaction; |
With sodium sulfate at 25℃; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
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With bromine |
Yield | Reaction Conditions | Operation in experiment |
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With phosphorus; hydrogen iodide at 140 - 150℃; im geschlossenen Rohr; | ||
With hydrogen iodide; hydrogen In acetic acid at 210℃; for 3h; Flow reactor; | 1 General procedure: General experimental procedure: Conduct the reaction in a Parr 300 milliliter (mL) High Pressure Hastelloy-C 276 Reactor, with a glass insert. Charge 90 mL of acetic acid (C2H4O2) into the reactor. Add a known amount of mucic acid (CeHioOs) to the acetic acid. Add HI 4 mL (55 % aqueous solution) to the reactor. Close the reactor and mount it on the reactor stand. Flush the reactor void space twice with nitrogen (200 psig,-1.38 megapascals, MPa) and release. Feed hydrogen to the reactor up to a pressure of 500 psig (~3.45 MPa), and heat under stirring (1000 revolutions per minute, rpm) to a temperature of 210 °C. Note reactor pressure on attaining the temperature and then increase up to 1000 psig (~6.89 MPa). Reaction commences as seen from a drop in the pressure of the reactor, and monitor against time. Continue the reaction in this fashion for a period of 3 hours. Fill with hydrogen intermittently to make up for the consumption of hydrogen in the reactor. Example 1 Using the above general experimental procedure, conduct the reductive dehydroxylation reaction of 0.07 moles of glucaric acid and 0.06 moles of HI in acetic acid solvent at a temperature of 210 °C for 3 hours. During the course of the reaction, observe a drop in the reactor pressure, which is indicative of the consumption of hydrogen. Analyze the liquid sample using nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography-mass spectroscopy (LC-MS). The LC-MS peak (mass-to-charge ratio based on negative ion) at 145 shows the presence of adipic acid (weight average molecular weight Mw 146) in the product. Calculate the conversion of the reaction using ]H NMR. Use the acetic acid -CH3 protons as an internal standard. After 3 hours, estimate the conversion to adipic acid at 40 %. |
Yield | Reaction Conditions | Operation in experiment |
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With permanganate(VII) ion at 0℃; | ||
With sulfuric acid Electrolysis; | ||
With dihydrogen peroxide |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
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bei der Einw.von Bac.coli unter anaeroben Bedingungen; | ||
With calcium carbonate bei der Einw.von Bact.lactis aerogenes unter anaeroben Bedingungen; |
Yield | Reaction Conditions | Operation in experiment |
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With water; dihydrogen peroxide; iron man faellt mit Phenylhydrazinacetat; bis-phenylhydrazone of melting point 242 degree-244 degree; |
Yield | Reaction Conditions | Operation in experiment |
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Durch Destillation; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; phosphoric acid; diethylene glycol at 135℃; |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid | ||
With nitric acid in mehreren Stufen; | ||
With iron(II) ammonium sulfate; disodium hydrogenphosphate; phosphoglucomutase; sucrose phosphorylase; myo-inositol monophosphatase; uronate dehydrogenase; myo-inositol 1-phosphate synthase; myo-inositol oxygenase; nicotinamide adenine dinucleotide oxidase; nicotinamide adenine dinucleotide; magnesium chloride In aq. buffer at 30℃; for 12h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; iron(II) sulfate at 30℃; for 1h; effect of reaction time, inhibitors (D-mannitol, thiourea, Me2SO), pH, buffers, further iron salt and complexing agents (EDTA, DTPA, ADP); experiments with a rat-liver microsomal preparation; | ||
With sodium hydroxide; sodium perchlorate; chloroamine-T at 35℃; for 24h; effect of reagents concentration, solvent isotope effect, Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.), also in solvents; effect of reaction products: p-toluensulphonamide and chloride ions; | ||
With dihydrogen peroxide; iron(II) sulfate at 30℃; for 3h; pH 6.0; |
With sodium hydroxide; sodium perchlorate; chloramine-B In water at 35℃; |
Yield | Reaction Conditions | Operation in experiment |
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1: 31% 2: 18% | With oxygen; sodium hydroxide In water at 60℃; for 24h; Autoclave; | |
1: 27% 2: 13% | With MoO5; dihydrogen peroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water at 60℃; for 18h; | General procedure for System 1 General procedure: The reactor (a 50 mL vial equipped with a Young valve and con-taining a stirrer flea) was charged with 0.25 M aqueous [MoO5](100 L, 2.5 mol% of glucose), the solvent [41] (BmimPF6, 2 mL),the oxidant (30% aqueous H2O2, 340 L, 3 mmol) and -d-Glucose (Sigma Aldrich, 182 mg, 1 mmol), in the aforementioned order. Thereactor was sealed and the solution reacted with constant stirring(600 rpm) in a thermostated oil bath (60C) during 18 h. Upon com-pletion, the reactor was immediately cooled to 0C and the mixturewas extracted with H2O (3 × 2 mL) and filtered with 0.45 m nylonsyringe filter. The resulting solution was diluted in ultra-pure water(500 L of sample + 500 L of H2O) and analyzed by HPLC by usinga Hi-Plex H column (300 × 7.7 mm), a refractive index detector (Varian 360-LC) and MilliQ water as mobile phase. Conversion,selectivity and C balance were obtained from HPLC measurements |
With ammonium vanadate In sulfuric acid at 90℃; for 3h; activation energy; different concentrations of H2SO4; |
With oxygen; sodium nitrite In sulfolane; perchloric acid at 59.85℃; | ||
With Fe-doped TiO2-supported zeolite; air In water; acetonitrile at 30℃; for 1.5h; UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
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With oxygen In water at 55℃; further catalyst, further reagent, effect of further catalyst and reagent; |
Yield | Reaction Conditions | Operation in experiment |
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With oxygen In water at 49.9℃; initial rate of consumption, pH effect; |
Yield | Reaction Conditions | Operation in experiment |
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69.1% | With H(1+) resin Rexyn 100(H) In water for 3h; |
Yield | Reaction Conditions | Operation in experiment |
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With water bei der Destillation; |
Yield | Reaction Conditions | Operation in experiment |
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With water bei der Destillation; |
Yield | Reaction Conditions | Operation in experiment |
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With water bei der Destillation; |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
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With chloroform at 150℃; im Rohr; <d-saccharic acid >-β.β'-methylene ether α.α'-bis-methylene ether ester; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride at 150℃; unter Druck; |
Yield | Reaction Conditions | Operation in experiment |
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With calcium carbonate bei der anaeroben Vergaerung durch Bact. coli und. Bac. lactis aerogenes; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen bromide; bromine | ||
With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
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With bromine; calcium carbonate |
Yield | Reaction Conditions | Operation in experiment |
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With bromine |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
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at 35℃; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; ethanol; water Reagens 4:Isobutylalkohol; Eindampfen nach einigen Stunden unter 12 mm Druck bei 41-44grad Badtemperatur; |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid | ||
With water; nitric acid in mehreren Stufen; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium permanganate; water; sodium carbonate |
Yield | Reaction Conditions | Operation in experiment |
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With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
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With permanganate(VII) ion |
Yield | Reaction Conditions | Operation in experiment |
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66.9% | With hydrogen bromide; magnesium bromide at 120℃; for 3h; | 33; 38 Example 33 Add 300g of sulfolane, 6.4g of hydrogen bromide (48% by mass) and 3.1g of magnesium bromide into a 500mL agitated high-temperature and high-pressure reactor lined with polytetrafluoroethylene. The mass percentage of hydrogen bromide is 1.0 %, the mass percentage concentration of magnesium bromide is 1.0%; start stirring, then add glucaric acid, where the mass percentage concentration of glucaric acid is 4.0%; heat to 120°C, dehydration cyclization reaction for 3h; the reaction is over Then, it was cooled to room temperature, filtered (the solid phase and the filtrate were sampled and analyzed by HPLC, the total molar yield of 2,5-furandicarboxylic acid was 66.9%). The solid phase was crude 2,5-furandicarboxylic acid, which was recrystallized The 2,5-furandicarboxylic acid product is obtained, and the filtrate is reused after dehydration and impurity removal. |
58% | With benzenesulfonic acid for 0.0333333h; microwave irradiation; | |
52% | With toluene-4-sulfonic acid at 140℃; for 2h; |
39 %Chromat. | With 1-butyl-3-methylimidazolium hydrogen sulfate; sulfuric acid at 120℃; for 17h; | 2.4 Solid galactaric acid can be processed according to the disclosed methods, for example by mixing with 1-butyl-3-methyl-imidizolium hydrogen sulfate as an ionic liquid and sulfuric acid as an acid catalyst to initiate the dehydration reaction to FDCA. Conditions established in Example 1 above can be used for this step. Procedure: The following procedure is used for the production of FDCA from mucic (galactaric) and saccharic (glucaric) acids in the presence of ionic liquid as a reaction solvent. Drying of ionic liquid: Place desired quantity of ionic liquid (1-butyl-3-methylimidazolium sulfate) in a weighed 50 ml three-neck reaction vessel. Place a three-way glass valve on the middle neck of the vessel to control the reaction environment as under vacuum or at atmospheric pressure under inert gas. The second side neck is sealed with a glass stoppet The third neck is fitted with a rubber stopper fitted with flexible tubing connected to a nitrogen cylinder to allow flow of nitrogen purge gas into the vessel. Nitrogen purge limits contact of the ionic liquid with water which has a deleterious effect on the reaction. Once the vessel is sealed and purged, the vessel with ionic liquid is heated to 60°C under vacuum in a stirred oil bath and maintained at that temperature until bubbling within the ionic liquid ceases (typically 20 minutes). Cool the reaction vessel to room temperature and purge with nitrogen. Weigh to determine dry weight of ionic liquid added. Adding reagents to vessel: Weigh out the desired substrate (mucic acid or saccharic acid) in the quantity desired for the experiment (1 g substrate for each 5 g of ionic liquid in most experiments). Add the substrate to the ionic liquid by briefly removing the glass stopper on the three- neck vessel. Add sulfuric acid in an amount equal to one to three molar equivalents of the dicarboxylic acid substrate, also through the opening of the glass stopper on the three- neck vessel. Replace the stopper to minimize exposure of the reaction mixture to the atmosphere and watet. Reaction of substrate: Return the vessel to the oil bath set to the desired reaction temperature. Connect the flexible tubing to the nitrogen cylinder and the vacuum line to the three-way valve. Slowly bring the vessel under vacuum to an absolute pressure of less than 1.0 mm Hg; during the evacuation reduce pressure slowly to avoid bubbling and deposition of the reaction mixture on the vessel walls. Allow the reaction to proceed for the desired length of time (10-40 hr) at reaction temperature. Analysis: At certain points during reaction and at the end of reaction, samples were taken from the reaction mixture for analysis. The reaction sample was diluted for HPLC analysis in one of two ways: 1) the sample was neutralized with 1.0 M NaOH solution and then further diluted with water to solubilize the ionic liquid and all substrates and products (including FDCA as the sodium salt); or 2) the sample was directly dissolved in dimethyland the peak for FDCA elutes at 18 minutes. Use of external calibration standards allows the concentration of each species to be determined in the reaction sample. Results: Several experiments were conducted to convert saccharic acid and mucic acid to FDCA in the ionic liquid solvent. These experiments are summarized in Table 3 below. |
With sulfolane; sulfuric acid In toluene at 100 - 130℃; | 1-19 Technique 1 experiment steps are as follows: Use a 10L reactor (the device does not have a distillation tower, condenser, or phase separator), turn on the stirring (the stirring speed is 300r/min) and the reactor jacket to heat the steam,Add 5L of catalyst-reaction solvent solution to the dehydration cyclization reactor R (the mass concentration of the catalyst is 10wt%),0.5kg hexasonic acid (salt) (substrate concentration is0.1kg/L catalyst-reaction solvent solution),React at a reaction temperature of 100130 for 1548h;After the reaction is over, cool, sample, analyze by HPLC,After calculation, the molar yield of the product 2,5-furandicarboxylic acid is obtained; the reaction product is further neutralized with alkali, and the reaction solvent is recovered by vacuum distillation, and then crystallized,After recrystallization, 2,5-furandicarboxylic acid product is obtained. |
Yield | Reaction Conditions | Operation in experiment |
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With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
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With Amberlite IR-120 In water |
Yield | Reaction Conditions | Operation in experiment |
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With sodium hydroxide; chlorine; potassium bromide In water at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
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With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium bromide In methanol at 0℃; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; N-bromo-p-toluenesulfonamide; sodium perchlorate In water at 30℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 52 percent / p-toluenesulfonic acid monohydrate / 2 h / 140 °C 2: 68 percent / p-toluenesulfonic acid monohydrate / 3 h / Heating 3: 87 percent / methanol / 3 h / 20 °C | ||
Multi-step reaction with 4 steps 1: 52 percent / p-toluenesulfonic acid monohydrate / 2 h / 140 °C 2: 65 percent / PCl5 / 2 h / 90 °C 3: 90 percent / 2 h / Heating 4: 87 percent / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Eindampfen einer wss. Loesung unter vermindertem Druck 2: sodium amalgam |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Eindampfen einer wss. Loesung unter vermindertem Druck 2: water; sodium-amalgam; sulfuric acid / Erwaermen des Reaktionsprodukts mit Methanol und wss. Salzsaeure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium disulfate | ||
Multi-step reaction with 2 steps 1: potassium disulfate 2: 40 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Eindampfen einer wss. Loesung unter vermindertem Druck 2: 100 °C | ||
Multi-step reaction with 2 steps 1: Eindampfen einer wss. Loesung unter vermindertem Druck 2: 100 °C | ||
In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen at 40℃; | ||
With oxygen at 40 - 70℃; | ||
With oxygen at 40℃; |
With oxygen at 40℃; |
Yield | Reaction Conditions | Operation in experiment |
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With sulfuric acid In water; acetone at 20℃; for 5.5 - 6.5h; Heating / reflux; | 1 EXAMPLE 1 Sulfuric acid (50.0 g, 0.500 mole) was added over a period of 30minutes to a stirred suspension of calcium D-glucarate tetrahydrate(160.15 g, 0.500 mole) in 500 mL of 95:5 acetone-water (prepared bymixing 475 mL of acetone with 25 mL of water).The stirred mixture was heated at reflux for 4 hours, allowed to coolto room temperature (20-25 °C), stirred at room temperature for 1-2 hours,and then filtered with suction to remove the precipitated calcium sulfate.At no time did the reaction become homogeneous. The precipitate waswashed three times with 150 ml_ of 95:5 acetone-water, each timesuspending the precipitate in the solvent and then sucking the solventthrough.Acetone was removed from the combined filtrate and washings bydistilling under reduced pressure (pot temperature 30 °C). Theconcentrated aqueous solution was stirred mechanically with a stream ofdry nitrogen passing through and over the surface of the solution. Thesolution was then heated to 120-130 °C for 2-3 hours, with continuedstirring and nitrogen-sparging, to remove water.Stirring and sparging was then discontinued, and the reactionmixture was allowed to cool to room temperature. The glassy product(85% yield, 92-94% pure) may be further purified by recrystallization.Analysis was performed by 1H NMR and by GC (silylation with BSTFA-TMSCI, J&W DB-17MS 30 m x 0.32 mm x 0.25 m column, oventemperaturel20-300 °C). |
Yield | Reaction Conditions | Operation in experiment |
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In water dissolving of NaVO3 in water under Ar atmosphere; treatment with D-saccharic acid at 1:1.2 VO2(V)-acid ratio at pH 2.61 - 8.10; monitoring by NMR; |
Yield | Reaction Conditions | Operation in experiment |
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In water in alkaline aq. soln.; monitoring by EPR, NMR and UV-Vis spectroscopy; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16 Chemical Conversion of Glucuronic Acid to Glucaric Acid Example 16 Chemical Conversion of Glucuronic Acid to Glucaric Acid The following method was used to convert glucuronic acid into glucaric acid. 5% Pd on carbon catalyst (10 g; 5% Pd/C catalyst; Johnson Matthey Inc., Ward Hill, Mass.) was placed in a 3-neck flask with 50 mL of distilled water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; oxygen In water at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid In water at 20℃; for 17h; | ||
With sulfuric acid In water; acetone at 20℃; for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dowex 50WX8-100 (H+) In water at 20℃; for 0.166667h; | 3.1.2. X-ray quality, crystalline d-glucaric acid (2) Monopotassium d-glucarate (1) was treated with Dowex 50WX8-100 H+ form ion-exchange resin as above and following removal of the resin by filtration, the combined filtrate was concentrated. The syrupy residue was seeded with a crystal from above and stored at 4 °C for 12 h. The crystals were removed from the flask, washed, quickly, with 97% ethanol and the fine solid and ethanol were removed with a pipette to afford X-ray quality, crystalline d-glucaric acid: mp 119.3 °C (lit.refPreviewPlaceHolder8 Y. Hirasaka, K. Umemoto, M. Sukegawa and I. Matsunga. Chem. Pharm. Bull., 13 (1965), pp. 677-680. 8 117-118 °C, lit.refPreviewPlaceHolder7 125-126 °C); +5.7 (c 0.064, D2O, 5 min.) [lit.refPreviewPlaceHolder8 +6.1 (c 1.0, H2O, 5 min), lit.refPreviewPlaceHolder7 +6.9 (c 1.0, H2O); 1H NMR (D2O): δ 4.48 (d, 1H, H2, J2,3 = 3.00 Hz), 4.36 (d, 1H, H5, J4,5 = 5.14 Hz), 4.14 (dd, 1H, H3, J2,3 = 3.00 Hz, J3,4 = 5.87 Hz), 4.00 (m, 1H, H4). 13C NMR (150 MHz, D2O): δ 176.74 (C1), 176.43 (C6), 74.12 (C4), 72.47 (C2), 72.43 (C3), 72.26 (C5); IR (KBr): 3492-2917 (s, O-H stretch), 1729 (s, CO stretch), 1692 (s, CO stretch) cm-1. | |
With Amberlyst H+ ion-exchange resin In water-d2 at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.2 g | Stage #1: D-glucaric acid With potassium hydroxide In water Stage #2: With hydrogenchloride In water Cooling with ice; | 4.9. Monopotassium d-glucarate isolation from an oxidation where nitric acid was evaporatively removed at reduced pressure with heat The pH of the concentrated reaction mixture from the oxidation of d-glucose (4:1 molar ratio of nitric acid to d-glucose) reconstituted with water (370 mL) was adjusted to a constant pH of 9.5 with 45% KOH. The solution was cooled in an ice bath and titrated to pH 3.4 with concentrated hydrochloric acid. A precipitate was formed when the solution pH dropped below 5. The mixture was cooled and held at 5 °C for 4 h and the precipitate then isolated by filtration. The resulting solid cake was washed with cold water and dried at reduced pressure for 18 h to give solid monopotassium d-glucarate (3), 83.2 g (45% yield from 134.3 g of dextrose). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With calcium chloride In dimethyl sulfoxide for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen In water; acetonitrile at 30℃; for 0.166667h; UV-irradiation; | liquid-phase photocatalytic selective oxidation of glucose The reaction system was stirred magnetically at 700 rpm to get a uniform suspension of the catalyst in the solution. A medium pressure 125 W mercury lamp (λmax = 365 nm) supplied by Photochemical Reactors Ltd. (Model RQ 3010) was placed inside the quartz immersion well as light irradiation source. The reaction temperature was established at 30 °C. Glucose solutions (2.8 mM) were prepared in a mixture of Milli-Q water and acetonitrile (ACN) (10:90, v/v) unless otherwise specified. Experiments were carried out from 150 mL of mother solution and a concentration of 1 g/L of the catalyst was used. All reactions were carried out under ambient air (no oxygen bubbling conditions). Approx. 2 mL of samples were taken from the photoreactor at pre-specified periods of time and were filtrated (0.20 μm, 25 mm φ nylon filters) in order to remove TiO2-supported particles before HPLC analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; sodium hydroxide In water at 60℃; for 0.383333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium trichloride; perchloric acid; acetic acid; 1,3-dichloro-[1,3,5]triazinane-2,4,6-trione In water at 35℃; | General procedure: All kinetic measurements were performed underpseudo-first order conditions with higher concentrationsof substrates compared to the oxidant.Dichloroisocyanuric acid (DCICA) was purchasedfrom Fluka. Inositol, sorbitol, mannitol, rutheniumchloride and all other chemicals used were of analyticalgrade and were obtained from SD Fine Chemicals.Essential volumes of oxidant and substrate solutionswere thermostated at 35 ± 0.1°C to attain equilibrium. After rapid mixing an equal volume of oxidant solutionto the substrate solution, progress of the reaction wasfollowed by assaying aliquots of the reaction mixturefor dichloroisocyanuric acid, iodometrically usingstarch as an indicator after suitable time intervals. Firstorder rate constants were evaluated from the linear plots(r2 > 0.997) of log[unreacted DCICA] against time. Allreactions were generally carried out in duplicate andthe rate constants were to ±2%. The concentration ofunreacted DCICA was determined by iodometry atpH 1-2 in order to follow the reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 35% 2: 17% 3: 7% | With dihydrogen peroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water at 60℃; for 18h; | General procedure for System 1 General procedure: The reactor (a 50 mL vial equipped with a Young valve and con-taining a stirrer flea) was charged with 0.25 M aqueous [MoO5](100 L, 2.5 mol% of glucose), the solvent [41] (BmimPF6, 2 mL),the oxidant (30% aqueous H2O2, 340 L, 3 mmol) and -d-Glucose (Sigma Aldrich, 182 mg, 1 mmol), in the aforementioned order. Thereactor was sealed and the solution reacted with constant stirring(600 rpm) in a thermostated oil bath (60C) during 18 h. Upon com-pletion, the reactor was immediately cooled to 0C and the mixturewas extracted with H2O (3 × 2 mL) and filtered with 0.45 m nylonsyringe filter. The resulting solution was diluted in ultra-pure water(500 L of sample + 500 L of H2O) and analyzed by HPLC by usinga Hi-Plex H column (300 × 7.7 mm), a refractive index detector (Varian 360-LC) and MilliQ water as mobile phase. Conversion,selectivity and C balance were obtained from HPLC measurements |
With oxygen; potassium hydrogen phthalate In water for 3h; UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With nitric acid at 60℃; for 1.5h; | |
60% | With 2.44 wt.% platinum and 2.38 wt.% aurum on carbon; oxygen In water monomer at 90℃; for 5h; | 2.B.ii Oxidation of Glucose to Glucaric Acid (Protocol 2) Suitably concentrated aqueous solutions of K2Pt(OH)6 and CsAu02 were added together to carbon black powders by incipient wetness impregnation and agitated to impregnate the supports. The samples were dried in an oven at 40°C overnight, and reduced at 250°C under a forming gas (5% H2 and 95% N2) atmosphere for 3 hours with 5 °C/min temperature ramp rate. The final catalysts were washed with deionized water and finally dried at 40°C to produce catalysts with a composition of 2.44 wt.% Pt and 2.38 wt.% Au. By using other carbon black supports, Au and Pt precursors, and adjusting amount of Au and Pt in solution, different catalysts with various Au and Pt loadings on a variety of commercial carbon black powders or particles from extrudates were prepared in a similar manner. These catalysts were tested for glucose oxidation using the following testing protocol. Catalyst (10 mg) was weighed into a glass vial insert followed by addition of an aqueous glucose solution (250 μ of 0.55 M). The glass vial insert was loaded into a reactor and the reactor was closed. The atmosphere in the reactor was replaced with oxygen and pressurized to 618 kPa (75 psig) at room temperature. Reactor was heated to 90°C and maintained at the respective temperature for 5 hours while vials were shaken. After that, shaking was stopped and reactor was cooled to 40°C. Pressure in the reactor was then slowly released. The glass vial insert was removed from the reactor and centrifuged. The solution was diluted with deionized water and analyzed by ion chromatography to determine the yield of glucaric acid and the selectivity as defined herein. Results are presented in Table 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium perrhenate; phosphoric acid; palladium on activated charcoal; hydrogen; pyrographite; at 150℃; under 3878.71 Torr; | General procedure: The table above demonstrates the significant yield improvements achieved by the addition of charcoal. The yield of adipate was improved to 91% from 70% by addition of activated charcoal, while the same ease of use (no atmosphere exchange, all reactions to the adipate carried out under the same set of conditions) was maintained. The catalyst system is also competent in the transformation of other diols in ctj3-position to carboxylate moieties as demonstrated in the table above. The final example in the table, i.e., 1,5-gluconolactone, demonstrates this selectivity within a single molecule: only the ctj3-diol group is transformed. The other hydroxy functionalities are not affected.[0136] A Parr reactor charged with polyol (7.5 mmol), KReO4 (22 mg), 10% Pd/C (60 mg), 85% H3P04 (26 mg), granular activated carbon (450 mg, C270C, purchased from Fisher), and MeOH (7.5 mL) was pressurized to 75 psi with H2. The reaction was placed in a preheated oil bath set to 150C for a given amount of time until the reaction was complete (typically from a few hours up to three days). The reaction mixture was cooled to room temperature, filtered, rinsed with MeOH, and concentrated |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iron(III) chloride; dihydrogen peroxide In water at 20℃; for 4h; Irradiation; | 2.4. Photocatalytic oxidation of glucose General procedure: In a typical photocatalytic reaction, 30 mg H-ZSM-5/FePz(SBu)8photocatalysts were firstly dispersed into 30 mL 3 mmol L1 aqueousglucose solution in a Pyrex vessel with a circling water-cooledjacket by ultrasonication for 5 min. Then an additional H2O2 with a H2O2:glucose ratio of 3.3:1 was added into the above suspensionand continually stirred for 10 min. After that, the reaction mixturewas irradiated by a Xe lamp (Bejing China Education Au-light Co.,Ltd) with a 420 nm cutoff filter. In order to control the photocatalytic reaction at ambient temperature, the cooling water was circulated through the circling water-cooled jacket located aroundthe reactor. Sample solutions were taken at specific times and then immediately filtered by 0.22 μm membranes before analyses. The glucose conversion and the selectivity of oxidation productwere monitored using a Dionex UltiMate 3000 HPLC system equipped with a refractive index (RI) (ERC RefractoMax520) detector,a Shodex SUGAR SH-1011 column (8 mm x 300 mm) and an aqueous 0.4 mmol L-1 H2SO4 solution as an eluent with a flow rateof 0.6 mL min1 were used. The products generated during thereaction were identified by comparison with standard samplesand further confirmed by high performance liquidchromatography-mass (HPLC-MS). HPLC-MS analysis was performedon a Shimadzu LCMS-8050 triple quadrupole mass spectrometerwith C18 column (4.6 mm 250 mm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | With tin(IV) chloride In water; toluene at 200℃; for 2h; Autoclave; High pressure; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 59.6% 2: 8.7% | With tin(IV) chloride In water; toluene at 200℃; for 1h; Autoclave; High pressure; Sealed tube; Inert atmosphere; | |
1: 47.2% 2: 14.3% | With tin(IV) chloride In water at 160℃; for 1h; Autoclave; High pressure; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.1% | With tin(IV) chloride In water at 200℃; for 1h; Autoclave; High pressure; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lanthanum orthoferrite In water monomer at 154.84℃; for 5h; Sealed tube; | 2.4. Batch reaction procedure General procedure: A CWAO of 1 wt% D-glucose water solution was tested in a 300 mlbatch stirred reactor (Parr Instruments Company, 4566 model). In atypical experiment, a catalyst loading of 15 mol.% was set during thereaction; about 100 mg of fresh catalyst was added to 50 ml of solutionin all the catalytic tests. After sealing the reactor head, air was allowedto flow into the reactor headspace, as described in Ref. [38]. Beforeheating, the reactor was pressurized with air at 5 bar; 1 bar of partialoxygen pressure was maintained inside the chamber.Afterwards, the reactor was heated up until the desired temperaturewas reached, according to the experimental set point. The temperaturesand pressures of the system were recorded each minute with an acquisitionsoftware supplied by the Parr Instruments Company. The experimentswere carried out at the desired temperature set point and for thedesired duration; subsequently, the system was quickly cooled at roomtemperature, in order to stop the reaction and to carry out the productanalysis as soon as the test had finished [39]. At the end of the test, thecatalyst was separated through a filtration and the liquid phase wasprepared for analysis; the solid residue was washed 5 times with distilledwater and dried overnight at 353 K to remove physisorbed water; then itwas weighed and stored. The blank test was performed by adding about100 mg of SiO2 to the mother solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lanthanum orthoferrite In water monomer at 154.84℃; for 5h; Sealed tube; | 2.4. Batch reaction procedure General procedure: A CWAO of 1 wt% D-glucose water solution was tested in a 300 mlbatch stirred reactor (Parr Instruments Company, 4566 model). In atypical experiment, a catalyst loading of 15 mol.% was set during thereaction; about 100 mg of fresh catalyst was added to 50 ml of solutionin all the catalytic tests. After sealing the reactor head, air was allowedto flow into the reactor headspace, as described in Ref. [38]. Beforeheating, the reactor was pressurized with air at 5 bar; 1 bar of partialoxygen pressure was maintained inside the chamber.Afterwards, the reactor was heated up until the desired temperaturewas reached, according to the experimental set point. The temperaturesand pressures of the system were recorded each minute with an acquisitionsoftware supplied by the Parr Instruments Company. The experimentswere carried out at the desired temperature set point and for thedesired duration; subsequently, the system was quickly cooled at roomtemperature, in order to stop the reaction and to carry out the productanalysis as soon as the test had finished [39]. At the end of the test, thecatalyst was separated through a filtration and the liquid phase wasprepared for analysis; the solid residue was washed 5 times with distilledwater and dried overnight at 353 K to remove physisorbed water; then itwas weighed and stored. The blank test was performed by adding about100 mg of SiO2 to the mother solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / Heating 2: hydrogenchloride; phosphoric acid / water monomer; 2-methoxy-ethanol / 2 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: toluene / Heating 2.1: hydrogenchloride; phosphoric acid / water monomer; 2-methoxy-ethanol / 2 h / 140 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: toluene / Heating 2.1: hydrogenchloride; phosphoric acid / water monomer; 2-methoxy-ethanol / 2 h / 140 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 16 h / 20 °C 4.1: acetonitrile / 1 h / 20 °C / Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: toluene / Heating 2.1: hydrogenchloride; phosphoric acid / water monomer; 2-methoxy-ethanol / 2 h / 140 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 16 h / 20 °C 4.1: acetonitrile / 2 h / 20 °C |
Tags: 87-73-0 synthesis path| 87-73-0 SDS| 87-73-0 COA| 87-73-0 purity| 87-73-0 application| 87-73-0 NMR| 87-73-0 COA| 87-73-0 structure
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H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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