Synthesis of new amines for enhanced carbon dioxide (CO2) capture performance: The effect of chemical structure on equilibrium solubility, cyclic capacity, kinetics of absorption and regeneration, and heats of absorption and regeneration

Abstract This work focused on the synthesis of new tertiary amines by varying the alkyl chain length with/without hydroxyl group in the structure. The effect of chemical structure of newly synthesized tertiary amines; 4-(dimethylamino)-2-butanol (DMAB), 4-(dipropylamino)-2-butanol (DPAB), 4-(dibutylamino)-2-butanol (DBAB), 4-((2-hydroxyethyl)(methyl)amino)-2-butanol (HEMAB) and 4-((2-hydroxyethyl)(ethyl)amino)-2-butanol (HEEAB) were evaluated based on CO 2 equilibrium solubility and cyclic capacity, as well as rates and heats of CO 2 absorption and regeneration. The results showed that three amines (i.e. DMAB, HEMAB and HEEAB) had the highest CO 2 absorption capacity (0.88, 0.44 and 0.68 mol CO 2 /mol amine at 313 K temperature and 15 kPa CO 2 partial pressure), and cyclic capacity (0.52, 0.26 and 0.40 at 313–353 K temperature range, 15 kPa CO 2 partial pressure). These amines also had fast CO 2 absorption rate (0.082, 0.111 and 0.142 mol CO 2 /min) and CO 2 regeneration rate (0.512, 0.452 and 0.295 mol CO 2 /min) while maintaining low heat of CO 2 absorption (−34.17, −56.21 and −69.79 kJ/mol CO 2 ) and heat input of CO 2 regeneration (39.73, 60.48 and 72.44 kJ/mol CO 2 ). Based on these results, DMAB, HEMAB, and HEEAB can be considered to be promising amine components for blending for a post combustion CO 2 capture process.

[1]  Zhiwu Liang,et al.  CO2 absorption kinetics of 4-diethylamine-2-butanol solvent using stopped-flow technique , 2014 .

[2]  Teerawat Sema,et al.  Correlations for Equilibrium Solubility of Carbon Dioxide in Aqueous 4-(Diethylamino)-2-butanol Solutions , 2011 .

[3]  A. Benamor,et al.  Modeling of CO2 solubility and carbamate concentration in DEA, MDEA and their mixtures using the Deshmukh–Mather model , 2005 .

[4]  Paitoon Tontiwachwuthikul,et al.  Catalytic and non catalytic solvent regeneration during absorption-based CO2 capture with single and blended reactive amine solvents , 2014 .

[5]  Kazuya Goto,et al.  CO2 Capture by Tertiary Amine Absorbents: A Performance Comparison Study , 2013 .

[6]  Hallvard F. Svendsen,et al.  Heat of Absorption of Carbon Dioxide (CO2) in Monoethanolamine (MEA) and 2-(Aminoethyl)ethanolamine (AEEA) Solutions , 2007 .

[7]  Yuichi Fujioka,et al.  Synthesis and selection of hindered new amine absorbents for CO2 capture , 2011 .

[8]  Christine W. Chan,et al.  Recent progress and new development of post-combustion carbon-capture technology using reactive solvents , 2011 .

[9]  Geert Versteeg,et al.  Structure and activity relationships for amine-based CO2 absorbents-II , 2009 .

[10]  Edward S Rubin,et al.  A technical, economic, and environmental assessment of amine-based CO2 capture technology for power plant greenhouse gas control. , 2002, Environmental science & technology.

[11]  J. Carson,et al.  Enthalpy of solution of carbon dioxide in (water + monoethanolamine, or diethanolamine, orN-methyldiethanolamine) and (water + monoethanolamine + N-methyldiethanolamine) atT = 298.15 K , 2000 .

[12]  Alan E. Mather,et al.  Solubility of carbon dioxide in aqueous diethanolamine solutions at high pressures , 1972 .

[13]  Prachi Singh,et al.  Structure and activity relationships for amine based CO2 absorbents-I , 2007 .

[14]  E. S. Hamborg,et al.  Dissociation constants and thermodynamic properties of alkanolamines , 2009 .

[15]  Hallvard F. Svendsen,et al.  Capacity and Kinetics of Solvents for Post-Combustion CO2 Capture , 2012 .

[16]  S. Kazama,et al.  Synthesis and characterization of new absorbents for CO2 capture , 2013 .

[17]  Timothy E. Fout,et al.  Advances in CO2 capture technology—The U.S. Department of Energy's Carbon Sequestration Program ☆ , 2008 .

[18]  Teerawat Sema,et al.  Kinetics of Carbon Dioxide Absorption into Aqueous Solutions of4-(Diethylamino)-2-Butanol and Blended Monoethanolamine and 4-(Diethylamino)-2-Butanol , 2012 .

[19]  Paitoon Tontiwachwuthikul,et al.  Recent progress and new developments in post-combustion carbon-capture technology with reactive solvents , 2013 .

[20]  S. More SYNTHESIS OF MANNISH BASES OF THIOSEMICARBAZIDE AS DNA POLYMERASE INHIBITORS AND NOVEL ANTIBACTERIAL AGENTS , 2013 .

[21]  Teerawat Sema,et al.  Kinetics of CO2 absorption into a novel 1-diethylamino-2-propanol solvent using stopped-flow technique , 2014 .

[22]  Shuj Kobayashi,et al.  Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brønsted Acid−Surfactant-Combined Catalyst in Water , 1999 .

[23]  J. Kitchin,et al.  Chemical and Molecular Descriptors for the Reactivity of Amines with CO2 , 2012 .

[24]  Zhiwu Liang,et al.  Solubility, absorption heat and mass transfer studies of CO2 absorption into aqueous solution of 1-dimethylamino-2-propanol , 2015 .

[25]  D. Savage,et al.  Gas treating with chemical solvents , 1983 .

[26]  R. Idem,et al.  Synthesis, solubilities, and cyclic capacities of amino alcohols for CO2 capture from flue gas streams , 2009 .

[27]  Sung Chan Nam,et al.  Solubility of CO2 in Aqueous Methyldiethanolamine Solutions , 1997 .

[28]  Graeme Puxty,et al.  Carbon dioxide postcombustion capture: a novel screening study of the carbon dioxide absorption performance of 76 amines. , 2009, Environmental science & technology.

[29]  J. E. Crooks,et al.  Kinetics of the reaction between carbon dioxide and tertiary amines , 1990 .

[30]  Geert Versteeg,et al.  On the kinetics between CO2 and alkanolamines both in aqueous and non-aqueous solutions—II. Tertiary amines , 1988 .

[31]  Yuichi Fujioka,et al.  Development of novel tertiary amine absorbents for CO2 capture , 2009 .

[32]  Hallvard F. Svendsen,et al.  Prediction of the pKa values of amines using ab initio methods and free-energy perturbations , 2003 .

[33]  Ji-Ho Yoon,et al.  Solubility of Carbon Dioxide in Aqueous Solutions of 2-Amino-2-methyl-1,3-propanediol , 1998 .

[34]  Hari C. Mantripragada,et al.  The outlook for improved carbon capture technology , 2012 .

[35]  Christine W. Chan,et al.  A statistical analysis of the carbon dioxide capture process , 2009 .

[36]  Zhiwu Liang,et al.  13C NMR Spectroscopy of a Novel Amine Species in the DEAB–CO2–H2O system: VLE Model , 2012 .

[37]  T. L. Donaldson,et al.  Carbon Dioxide Reaction Kinetics and Transport in Aqueous Amine Membranes , 1980 .