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11 amino alcohol 1-dimethylamino-4,4-dimethyl-3-pentanol (87g,55%)asacolorlessoil:bp 120°C./15mmHg; IR(neat) 3260(br),2954,1460cm“;1HNMR (CDCl3,500MHZ)6 3.38 (dd, 1:25, 10.5 HZ, 1H), 2.63 (dt, J:2.4, 12.2 HZ, 1H), 2.42(dt,1:29,12.0HZ,1H),2.22(s,6H),1.46-1.57(m,1H), 1.36-1.44(m,1H),0.85(s,9H);l3CNMR(CDCl3, 125MHZ) 6 81.4 (CH), 59.4 (CH2), 44.9 (CH3), 34.3 (C), 26.3 (CH2), 12 -continued 25.4(CH3). O Example 8 Synthesis of the amino alcohol 4-propylamino-2-butanol(8) 10 20 25 ExpansionoftheprotocolinExample 1to4-(ethyl-me thyl-amino)-2-butanol (9) Was accomplished by simply changing the diethyl amine to N-ethylmethylamine. To an ice-Water cold solution of neat N-ethylmethylamine (50 g, 0.85mol),freshlydistilledmethylvinylketone(76mL, 0.93 mol) Was added. After the addition Was completed in 1 hour, cooling Was removed and the reaction mixture Was stirred at room temperaturefor3hours.ItWas thendilutedWith50mL of methanol and cooled in an ice-Water bath. Sodium boron hydride (18 g, 0.46 mol) Was added portionWise. After the additionWascompletedin1hour,theice-WaterbathWas removed. The reaction mixture Was continuously stirred at roomtemperaturefor3hours,atWhichtime20mL ofsatu rated sodium chloride Was added, folloWed by another 30 minutes of stirring. The solid formed Was ?ltered through a shortpadofCeliteTMandWashedWithdichloromethane.The ?ltrate Was concentrated under reduced pressure. The con centrated solution Was diluted With diethyl ether, dried With Na2SO4, ?ltered and concentrated under reduced pressure. TheremainingmaterialWaspuri?edbyfractionaldistillation togivetheaminoalcohol4-(ethyl-methyl-amino)-2-butanol (71.8 g, 65%): bp 810 C./12 mmHg; IR (neat) 3282 (br.), 2962,1462,1125cm_l;1HNMR (CDCI3,500MHZ)63.85 (tq,1:25, 6.5 HZ, 1H), 2.59 (ddd, 1:40, 110,125 HZ, 1H), 2.45(ddd,J:7.0,12.0,14.5HZ,1H),2.40(dt,1:45,12.0HZ, 1H),2.25(dq,1:70,12.5HZ,1H),2.15(s,3H),1.46-1.55(m, 1H),1.35-1.42(m,1H),1.06(d,1:65HZ,3H),0.98(t,1:70 HZ,3H);13CNMR (CDCI3,125MHZ)669.9(CH),57.0 (CH2),51.7(CH2),41.5(CH3),34.1(CH2),23.7(CH3),12.4 (CH3). Example 10 Evaluation ofthe Performance ofAmino Alcohols (1)IO(9) (i)Apparatus: As can be seen in FIG. 1, the experimental apparatus con sistsofasaturationcell(tocontroltheconcentrationofsolu tion)connectedtoareactor(Lee,J.1.,Otto,F.D.andMather, A. E., “Equilibrium BetWeen Carbon Dioxide and Aqueous Monoethanolamine Solutions”, J.Appl. Chem. Biotechnol, Vol.26,pp.541-549, 1976).BoththecellandthereactorWere immersed in a constant temperature Water bath (Cole Par'mer)maintainedatindicatedtemperaturesWithanaccu racy of :0.01° C. stability by using a temperature controller (Cole-Parmer Polystat Immersion Circulators, Which oper ates Within the temperature range of —20 to 200° C.). The temperature in the system Was measured by a thermister (Cole-Parmer With an accuracy of :0.03° C.). (i)Materials: ThesolventsevaluatedWereMEAat99+%purity(ob tainedfromFisherscienti?c)andtheaminoalcoholssamples (1)to(9)describedinExamples 1to9,respectively.Aqueous solutionsoftheseamines/aminoalcoholsWereprepared using deioniZed Water to achieve a concentration of 3 mol/L ofsolution.NitrogenandCO2 (obtainedfromPraxairlnc.) — l. neat amine 2.NaBH4, MeOH ExpansionoftheprotocolinExample 1to4-propylamino 2-butanol (8) Was accomplished by simply changing the diethyl amine to propylamine. To an ice-Water cold solution ofneatpropylamine(82mL,1.0mol),methylvinylketone30 WasaddeddropWise(82mL, 1.0mol)over2hours.Afterthe addition Was completed, the reaction mixture Was stirred at the same temperature for 1hour, and atroom temperature for 2hours.ItWasthendilutedWith50mL ofmethanoland cooledinanice-Waterbath.Sodiumborohydride(45g,1.2 35 mol) Was added portionWise. After the addition Was com pleted in 2 hours, the ice-Water bath Was removed. The reac tionmixture Was continuously stirredatroom temperature for 3hours,atWhichtime30mL ofsaturatedsodiumchloride Wasadded,folloWedbyanother30minutesofstirring.The 40 solid formed Was ?ltered through a short pad of CeliteTM and Washed With dichloromethane. The ?ltrate Was concentrated under reduced pressure. The concentrated solution Was diluted With dichloromethane, dried With Na2SO4, ?ltered and concentrated under reduced pressure. The remaining 45 material Was puri?ed by fractional distillation to give the amino alcohol 4-propylamino-2-butanol (35.7 g, 27%): bp 1050 C./12 mmHg; IR (neat) 3282 (br.), 2962, 1462, 1125 cm_l;1HNMR (CDCI3,500MHZ)63.91(dtd,1:25,6.5, 15.0HZ,1H),2.92(ddd,1:40,5.0,12.5HZ,1H),2.69(ddd,50 1:35, 11.0, 12.0 HZ, 1H), 2.50-2.60 (m, 1H), 2.40-2.48 (m, 1H),1.38-1.54(m,4H),1.09(d,1:65HZ,3H),0.85(t,1:75 HZ,3H);13CNMR (CDCI3,125MHZ)669.9(CH),51.7 (CH2),49.1(CH2),36.9(CH2),23.8(CH3),23.2(CH2),12.0 (CH3) Example 9 Synthesis of the amino alcohol 4-(ethyl-methyl-amino)-2-butanol(9) v1 l.N-ethylmethylamine 2.NaBH4, MeOH 55 65 MN/V H 8 US 7,910,078B2PDF Image | METHOD OF CAPTURING CARBON DIOXIDE FROM GAS STREAMS
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