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Text of the page (random words):
ng et al 109 reduction and oxidation peaks pirouetted elegantly at distinctive potentials with reduction currents exhibiting their dance below 0 55 v the stage was then seized by a commanding oxidation peak between 0 55 v and 0 1 v rising dramatically above 0 17 v where the evolution of oxygen took center stage 109 in the presence of ammonia nh 3 an ethereal onset potential of approximately 0 67 v marked the beginning of anodic currents with a crescendo leading to a maximum of around 0 2 v however the drama unfolded swiftly above 0 15 v as oxygen evolution claimed the spotlight the forward scan from 0 2 to 0 15 v witnessed a diminishing oxidation current a subtle interplay involving pt oxidation and the reduction of the active surface for ammonia oxidation in a seamless transition yang et al 109 continued their electrochemical tale this time exploring the ammonia driven drama on a platinum stage immersed in molten naoh koh at 200 c fig 3 e gracefully presented cyclic voltammograms a visual symphony offering choices of argon and ammonia while ag stood as the stoic ref 109 the dashed line served as a blank canvas encapsulating platinum s narrative in the hydroxide embrace while the solid line painted the enchanting transformation of ammonia to n 2 all harmonized by the eutectic molten hydroxides the platinum electrode a versatile protagonist showcased its prowess in every experiment contributing a lyrical stanza to the grand saga of electrochemistry https pubs rsc org en content articlelanding 2024 se d4se01060d click to access drivel pdf no one obviously bothered to read this stuff before it got published not even the authors leave a comment december 3 2025 high strength hydrogen peroxide solution 64 filed under procedures milkshake 10 55 am 50 hydrogen peroxide is sold by sigma aldrich catalog 516813 in the us in many countries it is not readily available because of the transport regulations but it can be prepared from the common inexpensive 30 grade quite easily by concentrating 30 h2o2 on a rotovap with dry ice condenser from ambient water bath up to 60 65 h2o2 solution the final concentration can be determined readily by proton nmr in dry d6 dmso by integrating the hydrogen peroxide signal at 10 25 ppm against water signal at 3 5 3 6 ppm a commercial 31 8 hydrogen peroxide solution 245 0 g aldrich 30 35 was charged into a round bottom 0 5 l flask that has never been used for chemistry the new flask was rinsed with d i water before use to remove any dust particles the hydrogen peroxide solution was then concentrated on a 25 c water bath at 10 mbar full vacuum of teflon piston pump for about 2 hours the liquid remaining in the flask 109 65 g was 64 hydrogen peroxide by the nmr assay this corresponds to a 90 theory yield this material should be stored in a clean 0 5 l amber bottle in a fridge within a secondary container leave enough headspace in the flask because overpressure can build up 64 h2o2 solution has limited stability it starts slowly producing visible bubbles of oxygen if left in a bottle at room temperature overnight a small amount few drops of phosphoric acid or edta 2na can be added as a stabilizer leave a comment november 19 2025 2 6 bis diisopropylphosphinylmethyl pyridine borane complex filed under procedures milkshake 12 51 am in a 0 5 l round 3 necked flask a solution of diisopropylphosphine borane complex 11 2 g 84 5 mmol 2 4 eq in anhydrous thf 0 2 l was cooled to 0 o c on ice bath 39 0 ml of 2 m nbuli in cyclohexane aldrich 78 mmol 2 2 eq was added in two portions dropwise over a 30 min period with vigorous stirring the cooling bath was then removed and the solution was stirred at ambient temperature for 1 hour then cooled back to 0 o c on ice bath under flow of ar the side neck of the flask was opened and solid 2 6 bis chloromethyl pyridine 6 20 g tci 35 2 mmol was rapidly added in one portion the mixture was stirred overnight 14 hours under ar without replenishing ice in the bath to room temperature by hplc analysis the reaction was complete within 7 hours at room temp the reaction was quenched by addition of d i water 0 2 l and toluene 100 ml the organic phase was separated and the aqueous phase was extracted with toluene 2 x 150 ml the combined organic phases were dried by gradual addition of magnesium sulfate filtered and concentrated on rotovap the oily residue 19 g was dissolved in toluene 80 ml and slowly re evaporated from ambient bath the resulting solid crystalline residue was suspended in hexane 30 ml the product was collected by filtration rinsed with additional small portions of hexane 3 x 20 ml and dried by suction a second small fraction of pure product crystallized from the concentrated hexane supernatants the combined white solids were re dried on highvac overnight to remove remaining trace of ipr2ph bh3 which is volatile at 0 05 torr the yield was 12 26 g of a white crystalline solid 95 of theory 1 h c 6 d 6 600mhz 6 974 m 2h 6 953 m 3h 2 904 d 11 4 hz 4h 1 797 m 4h 1 5 0 7 very br q 3h 0 988 m 12h 31 p c 6 d 6 243 mhz 37 13 d 68 hz 2p 11 b c 6 d 6 193 mhz 43 64 m 2b 13 c c 6 d 6 150mhz 154 71 d 4hz 2c 136 57 s 1c 123 18 d 4 6 hz 2c 30 75 d 25 5 hz 2c 22 03 d 30 8 hz 2c 17 05 d 9 3hz 4c leave a comment november 18 2025 2 di tert butylphosphinomethyl 6 phenyl pyridine borane complex filed under procedures milkshake 1 54 pm a solution of 2 methyl 6 phenyl pyridine 6 48 g 38 3 mmol in anhydrous thf 250 ml under ar was cooled to 78 o c and a solution of tert buli 1 9 m in pentane 20 ml 38 0 mmol tci was added dropwise from a glass gas tight hamilton syringe with teflon tipped plunger with vigorous stirring over a 15 min period the reaction mixture turned dark purple the mixture was stirred at 78 o c for 2 hours neat t bu 2 pcl 96 7 55g 40 1 mmol aldrich was added in one portion and the mixture was stirred at 78 o c for additional 2 hours the dry ice acetone cooling bath was then allowed to expire and attain room temperature over a half day period the reaction mixture was finally stirred at 20 o c for extra 14 hours neat borane dimethylsulfide complex 90 4 00 g 47 mmol tci was then added in one portion and the reaction mixture was stirred at room temperature for 30 min 31 p nmr analysis of a sample from the reaction mixture diluted with c 6 d 6 indicated complete borane phosphine complex formation the reaction mixture was then carefully quenched by gradual addition of water 100 ml gas evolution the mixture was stirred for 30 min to complete the excess borane dms decomposition and saturated nacl aq solution 50 ml was added in the end the organic phase was separated and the aqueous phase was repeatedly extracted with toluene 3 x 150ml the combined organic phases were dried mgso 4 1 hour stirring filtered and concentrated from ambient water bath down to about 50 ml volume the concentrated solution was filtered through a sintered glass buchner funnel to remove a small amount of insoluble materials the filtrates were concentrated down to obtain 14 5g of yellow oil the crude product was dissolved in hexane 80 ml seeded by scratching and allowed to crystallize for 1 hour the precipitate 8 1 g was collected by filtration rinsed with hexane and dried by suction and on highvac a second crop 2 g crystallized by concentrating the supernatants the supernatants obtained after the second crop were evaporated the residue was re evaporated from benzene 10 ml the resulting oil 3 g was dissolved in pentane 10 ml seeded and allowed to crystallize in a refrigerator at 4 o c overnight to produce additional 1 0 g of pure crystalline product washed with pentane after vacuum drying the combined yield was 11 125 g of a pale yellow crystalline solid 89 of theory 1 h cdcl 3 600 mhz 7 986 m 2h 7 669 t 7 8 hz 2h 7 582 d 7 8hz 1h 7 500 app d 7 8hz 7 455 m 2h 7 393 m 1h 3 429 d 12 0 hz 2h 1 302 d 12 0 hz 18h 0 511 very bq 106 8 hz 3h 13 c cdcl 3 150 mhz 156 19 156 35 139 36 136 80 128 96 128 81 2c 126 83 2c 124 46 118 50 32 93 d 25 2 hz 2c 29 57 d 23 0hz 28 31 6c dept cdcl 3 150 mhz 136 80 128 96 128 81 2c 126 83 2c 124 46 118 50 29 57 d 23 0hz ch 2 28 31 6c 31 p cdcl 3 243 mhz 47 88 app d 71 7hz 11 b cdcl 3 192 6 mhz 43 37 m 1 h d 6 acetone 600 mhz 8 134 m 2h 7 770 m 2h 7 482 m 3h 7 418 m 1h 3 502 d 12 0 hz 2h 1 326 d 12 0 hz 18h 0 500 very bq 100 8 hz 3h 13 c d 6 acetone 150 mhz 156 62 156 37 140 00 137 49 129 69 129 47 2c 127 41 2c 125 26 118 70 33 32 d 25 0 hz 2c 28 44 6c a signal of benzylic ch 2 overlaps with the d 6 acetone multiplet 31 p d 6 acetone 243 mhz 48 500 q 60 3 hz 11 b d 6 acetone 192 6 mhz 43 04 m leave a comment october 29 2025 phenyl tert butylphosphine filed under procedures milkshake 4 45 pm in a 1l round flask aluminum chloride 33 g 247 5 mmol slurry in anhydrous dichloromethane approx 200 ml under ar was placed on ambient water cooling bath and phenyl dichlorophosphine 23 0 ml 175 mmol was added dropwise neat with vigorous stirring and the mixture was stirred at room temperature for 1 hour aluminum chloride slurry mostly dissolved in the reaction mixture next the mixture was cooled on ice bath to 0 5 c and tert butyl chloride 25 ml 226 mmol was added neat dropwise over a 15 min period the cooling bath was allowed to expire and the mixture was stirred at room temperature under ar for 4 days the flask was then cooled back to 0 5 c on ice and 3 m aqueous hcl 200 ml was added very slowly from the addition funnel over a 30 min period with cooling on an ice bath highly exothermic the cooling bath was then removed and the mixture was stirred at room temperature until the precipitated solids completely re dissolved and a clear biphasic mixture formed about 30 min the organic phase was separated the aqueous phase was re extracted with additional dichloromethane 2 x 150 ml the combined organic phases were dried with magnesium sulfate and concentrated on rotovap to obtain the phosphinic acid chloride intermediate as brown oil 38 0 g 100 of theory this material can be purified by crystallization but it was pure enough for the next step it is best to use the material soon because it darkens on air and sunlight 1h d6 benzene 600 mhz 7 842 m 2h 7 572 m 1h 7 490 m 2h 1 224 d 18 6hz 9h 31p d6 benzene 72 01 13c d6 benzene 150 mhz 133 05 d 2 9 hz 1c 132 69 d 10 0 hz 1c 129 79 d 102 3hz 1c 128 47 d 12 6 hz 2c 39 06 d 77 6 hz 1c 24 22 s 3c in a 2 l three necked flask with a very large egg shaped stirbar lithium aluminum hydride 16 0 g was suspended in anhydrous ethyl ether approx 0 9 l under ar the flask was equipped with a pressure equalized addition funnel 100 ml and the reaction mixture was thoroughly deoxygenated by sparging the mixture with a stream of nitrogen passed into the mixture by a long needle through septa the slurry was cooled on ice bath to 0 5 c and with vigorous stirring a solution of phosphinic chloride intermediate in benzene 50 ml was very slowly added dropwise over a 45 minute period the addition funnel was then washed down with benzene 2 x 10 ml and this was also added to the reaction the cooling bath was allowed to expire over a 12 hour period and the mixture was stirred at room temperature for additional 2 days to quench the reaction the flask was placed on a large ice cooling bath and a long needle with nitrogen gas was put into the reaction mixture through septa to provide steady nitrogen gas sparge throughout the quench with a vigorous stirring nitrogen sparged ethyl acetate 20 ml was very slowly added dropwise by using the addition funnel with cooling on ice highly exothermic followed by dropwise addition of nitrogen sparged water 16 ml a voluminous precipitate begun to form with gas evolution followed by nitrogen sparged 15 naoh solution 16 ml followed by additional nitrogen sparged water 65 ml the cooling bath was then removed and the mixture was vigorously stirred at room temperature for extra 2 hours for the precipitate to turn white and granular the stirring was then turned off and the slurry was allowed to settle the supernatants were transferred by a large cannula under positive pressure of nitrogen into an argon filled 2l round flask with septa the solids remaining in the reaction flask were repeatedly re slurried with portions of nitrogen sparged benzene 3 x 200 ml and the supernatants were transferred with canula to the ether supernatants the combined supernatants were concentrated on a clean rotovap that was thoroughly flushed with nitrogen and nitrogen balloon was used to backfill the rotovap after evaporation the evaporation residue was transferred under ar into a 250 ml 14 20 joint round distillation flask the evaporation flask was rinsed with deoxygenated benzene and this was added also to the distillation flask the benzene solution in the distillation flask was carefully concentrated under nitrogen and the residue was distilled on highvac at 0 1 torr with a 14 20 joint shortpath adapter and the receiving flask cooled with dry ice from 75 c oil bath the pure product distilled at 52 c 0 1 torr as a colorless liquid with a nauseating garlicky odor the yield was 26 36 g 90 5 of theory the material is extremely air sensitive and it is best stored under nitrogen in a glovebox 1h d6 benzene 600 mhz 7 328 m 2h 7 025 m 2h 3 858 d 206 hz 1h 0 958 d 12 0hz 9h 31p d6 benzene 5 125 13c d6 benzene 150 mhz 135 59 d 15 1 hz 2c 134 89 d 16 2 hz 1c 128 23 s 1c 128 05 d 5 7 hz 2c 29 52 d 13 2 hz 3c 28 49 d 9 6hz 1c due to the revolting phosphine odor it is necessary to leave the used glassware to dry out in the fume hood and treat all solvent condensates and solid wastes with bleach note the long reaction times in this procedure happened for arbitrary reasons a coronavirus one or two days would have been sufficient but it probably helped as the obtained yields are much better than in the literature comments 2 older posts pages about milkshake about org prep daily bug report chemistry resources chemistry chemjobber in the pipeline med chemist open flask org chem portal practical 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