CO2 Capture Using Solutions of Alkanolamines and Aminosilicones

Article pubs.acs.org/EF

CO2 Capture Using Solutions of Alkanolamines and Aminosilicones Robert J. Perry* and Jason L. Davis GE Global Research, 1 Research Circle, Niskayuna, New York 12309, United States ABSTRACT: Tertiary amino alcohols have been shown to be effective co-solvents for CO2 capture when used in conjunction with aminosilicones. In some cases, they demonstrated a marked increase in CO2 capture compared to an equivalent weight loading of triethylene glycol and also showed a lower viscosity at a given CO2 loading. These materials may be useful as cosolvents in carbon capture processes using aminosilicones.

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agent or accelerate the decomposition of TEG itself.6 TEG has also been reported to decompose at relatively low temperatures.7 Alkanolamines were explored as another class of co-solvents that could not only solubilize the carbamate products and possess acceptable boiling ranges but may also decrease the viscosity and potentially achieve higher CO2 loadings. The higher loadings may be realized through several possible mechanisms, including greater physical absorption, interaction of the additional amine groups with CO2 and the hydroxyl functionality, or the ability of a tertiary amine to catalyze the hydrolysis of CO2 to form bicarbonate ions and protonated amine.8 Alkanolamines are also widely used in the oil and gas industry to sweeten crude products by removing sulfurcontaining materials, such as H2S,9 and are known to react rapidly with SO2.8,10 In this case, the alkanolamines may prolong the life of the more valuable aminosilicone solvent by preferentially reacting with sulfur contaminants. This ability, in addition to the increased buffering capacity of alkanolamines over TEG represents significant potential advantages when considering the development of a robust process. The simplest member of the alkanolamine class widely used for CO2 capture is monoethanol amine (MEA). However, this material has a relatively low boiling point (170 °C), which makes it undesirable for these applications, and we wished to have a co-solvent that did not participate in covalent CO2 absorption. Ideally, alkanolamine would allow for the solvent mixture to maintain liquidity in the presence of CO2, and aminosilicone carbamate salt would be thermally stable to 150 °C under absorption and desorption conditions and be commercially available on industrial scales.11 This paper describes some of the initial work using these solvents in concert with aminosilicones for post-combustion CO2 capture.

INTRODUCTION In the past decade, significant effort has been directed toward post-combustion capture of CO2 from coal-fired power plants. Numerous materials have been proposed as CO2 capture solvents, with many of them taking the form of aqueous solutions of organic amines.1 We recently reported on the use of aminosilicones as CO2 capture materials in conjunction with glycols, such as triethylene glycol (TEG).2 Use of this nonaqueous co-solvent permitted solubilization of the starting aminosilicone as well as the carbamate salt that was formed. The non-aqueous system also decreased the energy penalty associated with boiling water in the desorption process and, thus, provided a lower cost option for carbon capture. The high boiling point (or low vapor pressure) of any solvent system employed is highly desirable because this would mitigate solvent slip (volatilization) during the desorption process as well as decrease evaporation of the sorbent under the flow rate of flue gas anticipated in the absorber. TEG, a common solvent for high-temperature industrial processing, has a boiling point of 285 °C3 and an equally acceptable low vapor pressure.4 Similarly, many of the aminosilicones employed also possessed boiling points in excess of 250 °C. One drawback to the use of TEG was the increase in viscosity when the aminosilicone solution was exposed to CO2. The carbamate product readily formed hydrogen bonds within the solvent system and increased the solvent viscosity. The viscosity achieved during carbamate formation using GAP-0 was ∼1300 cP at 40 °C in a system fully loaded with CO2. While this is higher than that seen in aqueous amine systems, the higher viscosity does not pose a problem in the circulation of the solvent mixture and allows for more efficient CO2 capture as defined by the amount of CO2 captured per unit volume. These higher viscosities may negatively impact the mass- and heat-transfer capabilities of the solvent system and also elevate the risk of absorber column flooding. However, with the proper engineering controls, these issues can be successfully addressed and the advantages of higher CO2 loading and lower energy requirements found in a non-aqueous system can be realized. In addition, TEG is known to be hygroscopic,5 and absorption of even small amounts of water during the process may result in the acid conditions associated with high corrosion rates. Given the low buffering capacity of TEG, a lower pH may also result in the formation of heat-stable salts capable of poisoning the more expensive CO2 capture © 2012 American Chemical Society

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RESULTS AND DISCUSSION The optimal alkanolamine co-solvent would possess the lowest molecular weight possible while maintaining a high level of hydroxy functionality for solubility purposes, a low vapor pressure, a high boiling point, and a viscosity that still permitted facile liquid handling. Several materials of interest are shown in Received: December 15, 2011 Revised: February 15, 2012 Published: March 2, 2012 2512

dx.doi.org/10.1021/ef201963m | Energy Fuels 2012, 26, 2512−2517

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Table 1. Selected Physical Properties of Alkanolamine Co-solvents

Table 2. CO2 Uptake and Viscosity of GAP-0 Carbamate at 50 wt % in Alkanolamine Co-solvent entry

alkanolamine

CO2 uptake (wt %)

CO2 uptake (theoretical wt %)

CO2 uptake (% of theory)

carbamate solution viscosity (cP at 40 °C)

11 12 13 14 15 16 17 18 19

TEA MDEA DIPEA DEA TIPA DIPA DEPA DEPAD TEG

10.6 11.3 7.5 15.1 9.8 16.3 11.6 11.2 10.4

8.9 8.9 8.9 8.9 8.9 8.9 8.9 8.9 8.9

119 128 93 172 111 185 131 127 117

7300 2500 2800 50400 36600 399000 1200 6400 1250

theoretical uptake values were solely based on GAP-0 reacting with 1 mol of CO2 to generate the carbamate, as shown in eq 1.

Table 1. While several do not fit the profile above, they were included to provide a broader scope of the structure−property relationships. TEG is included for comparison. Alkanolamines in entries 3 and 9 possessed very low viscosities at 4 cP, and both had boiling points of ∼190 °C. A presence of a second hydroxyl group elevated the viscosity by a factor of 7 or more (entries 2 and 9). If amine was secondary and possessed a N− H bond, another substantial increase was noted (entry 4). Finally, triols gave even higher viscosities or remained solid at 40 °C (TEA, entry 1). To screen the efficacy of the alkanolamine co-solvents, preliminary CO2 absorption reactions were run at a 50:50 wt % of GAP-0/co-solvent. Table 2 shows the results of these experiments, which were run at 40 °C for 2 h with dry CO2 and mechanical stirring to ensure the complete reaction. The 2513


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Scheme 1. Alkanolamine as a Proton Acceptor

As seen in Table 2, all but one of the co-solvents (entry 13) permitted substantially greater than 100% weight increase. This was expected for the secondary amines in entries 14 and 16 because the N−H group can also chemically participate in CO2 absorption. With the other co-solvents, the greater than theoretical yield could be accounted for by tertiary amine acting as a proton acceptor, as shown in Scheme 1, or the production of a carbonate through the hydroxyl group, as seen in eq 2.17

Table 3. CO2 Capture by GAP-1 and 50 wt % Alkanolamine entry alkanolamine 20 21 22 23

DIPEA DEPA MDEA TEG

% CO2 absorbed

theoretical wt %

% of theory

viscosity (cP)

7.5 7.8 8.8 7.5

6.8 6.8 6.8 6.8

110 115 129 110

400 900 950 400

As expected, all of the aminosilicones reacted well in the cosolvent, with absolute weight gains up to 17.8% with the aminoethylaminomethyl derivative (GAP-AEAM) in entry 26. However, there was a general increase in the viscosity as the amount of CO2 captured increased, with entry 26 showing a viscosity >100 000 cP. A series of CO2 absorption experiments were also run with two alkanolamine co-solvents and GAP-1 in varying ratios. These data showed the trade-off between viscosity and CO2 loading. Tables 5 and 6 and Figure 1 illustrate the results for MDEA and DEPA. Also included are data for varying ratios of GAP-1 in TEG (Table 7). Figure 1 illustrates the linear relationship between CO2 loading and weight percent of GAP-1 and an exponential correlation with viscosity and the GAP-1 content. One can see that a large viscosity penalty is incurred going beyond 60−70 wt % aminosilicone. For a given ratio of GAP-1 in a co-solvent, the viscosities are very similar; however, there is a clear advantage of higher CO2 loadings when using MDEA at GAP1/co-solvent ratios at 50% or lower.

Either mechanism would account for the elevated increase in CO2 uptake. However, a control experiment in which CO2 was bubbled through N-methyldiethanolamine (MDEA) did not show any carbonate formation, as determined by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. While all of the GAP-0/alkanolamine solutions readily reacted with CO2, several had viscosities comparable to TEG (entries 12, 13, and 17), with one displaying a value slightly lower than the original TEG sample. The triols demonstrated much higher viscosities when fully reacted (entries 11 and 15), and the secondary amines formed extremely viscous liquids that were far outside any useful range for this application (entries 14 and 16). In all cases, the GAP-0 carbamate salt formed in these reactions solidified upon standing. This was expected because the same behavior was seen with TEG. However, when GAP-1 was tested with the three most promising alkanolamine cosolvents from Table 2, the carbamate products remained soluble for extended periods of time. Table 3 shows that viscosities less than 1000 cP for all three co-solvents were achieved with greater than 100% loading. MDEA was chosen as the optimal of the three solvents examined in Table 3 because of the higher boiling point and greater CO2 capture capacity. This co-solvent was then used to evaluate the effect on other aminosilicone capture solvents, as shown in Table 4.

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CONCLUSION Tertiary amino alcohols have been shown to be effective cosolvents for CO2 capture when used in conjunction with aminosilicones. In some cases, they demonstrated a marked increase in CO2 capture compared to an equivalent weight loading of TEG and also showed a lower viscosity at a given CO2 loading. These materials may be useful as co-solvents in carbon capture processes using aminosilicones. 2514


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Table 4. CO2 Capture by Aminosilicones and 50 wt % MDEA

Table 5. CO2 Uptake and Viscosity of GAP-1 Carbamate in Various Ratios of MDEA entry

ratio of GAP-1/MDEA

CO2 uptake (wt %)




30 31 32 33 34 35 36

20:80 30:70 40:60 50:50 60:40 70:30 80:20

5.1 6.4 7.2 8.8 9.1 11 12.2

2.7 4.1 5.4 6.8 8.2 9.5 10.9

188.9 156 133 129.1 111 115.8 112

130 240 450 950 1890 4880 16200

Table 6. CO2 Uptake and Viscosity of GAP-1 Carbamate in Various Ratios of DEPA entry

ratio of GAP-1/DEPA

CO2 uptake (wt %)




37 38 39 40 41 42

20:80 30:70 40:60 50:50 60:40 70:30

2 3.8 5.9 7.5 8.8 10.4

2.7 4.1 5.4 6.8 8.2 9.5

74 93 109 110 107 109

15 60 220 420 1550 4960

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liquid, and another tube connected to a bubbler filled with silicone oil. Each sample was heated to 40 °C (oil bath) for 2 h with gentle stirring. The CO2 flow was produced via charging 250−270 g of dry ice to a 1000 mL three-necked flask equipped with a stopper, a plastic tube connected through a drying tube (filled with blue Indicating Drierite) to the CO2 inlet on the 100 mL flask, and finally, a stopcock that was used to control the rate of gas flow through the test system. The rate was adjusted so that a steady stream of bubbles was observed in the bubbler. Care was taken to keep the flow from being excessive.

EXPERIMENTAL SECTION

All alkanolamines were obtained from commercial sources and used as received, as well as 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (GAP-0, entry 24) and 1,3-bis(2-aminomethylaminoethyl)-1,1,3,3tetramethyldisiloxane (GAP-AEAM, entry 26). General Procedure for Measuring CO2 Uptake. Samples of the aminosiloxane/co-solvent blend were charged to a 100 mL threenecked flask, and the mass was determined using an analytical balance. The flask was equipped with an overhead stirrer, a CO2 inlet terminating with a glass pipet aimed slightly above the surface of the 2515


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Figure 1. Viscosity and CO2 uptake as a function of the weight percent of GAP-1 in DEPA, MDEA, and TEG.

Table 7. CO2 Uptake and Viscosity of GAP-1 Carbamate in Various Ratios of TEG entry

ratio of GAP-1/TEG

CO2 uptake (wt %)




43 44 45 46 47 48 49

20:80 30:70 40:60 50:50 60:40 70:30 80:20

3.5 4.9 6.4 7.5 9.5 10.6 11.9

2.7 4.1 5.4 6.8 8.2 9.5 10.9

128 120 117 110 115 111 109

60 120 260 430 1300 3740 16200

When the test was complete, the CO2 flow was discontinued as was stirring. The sample was then cooled to room temperature, and the outside of the flask was wiped clean to remove any silicone oil remaining from the oil bath. After the outside of the flask was dried, the combined weight of the reaction vessel was determined using an analytical balance. The weight gain was then compared to the theoretical weight gain based on the amount of aminosiloxane charged, the number of amines per molecule, and the molecular weight of the material. It was assumed that two amines are required to react with each CO2 molecule (MW = 44.01) via the classic primary amine−CO2 reaction. Viscosity Measurements. Viscosities were determined using a Cannon-Fenske viscometer. The fluid being measured was added to the appropriate tube and allowed to come to 40.0 °C over 1 h in a temperature-controlled water bath. A series of three measurements were taken, and the average value is reported. 1,3-Bis(3-(2-aminoethyl)aminopropyl)-1,1,3,3-tetramethyldisiloxane (GAP-AEAP, Entry 27). Ethylenediamine (155 g, 2.58 mol) was charged to a 500 mL three-necked flask equipped with a magnetic stir bar, reflux condenser, addition funnel, and nitrogen sweep. It was then heated using an oil bath. Once the temperature reached about 95 °C, 1,3-bis(3-chloropropyl)-1,1,3,3-tetramethyldisiloxane, 20, (73 g, 254 mmol) was added dropwise over about 2 h. During this time, the temperature of the oil bath was allowed to increase to about 110−115 °C. Once addition was complete, the reaction mix was allowed to continue at this temperature for an additional 2 h, at which time 1H NMR indicated that the reaction was complete. The mix was cooled, and then some of the excess ethylene diamine was stripped off. At this point, the material was cooled to room temperature and partitioned between chloroform and 10% NaOH, and then the organic phase was washed with deionized water and saturated sodium chloride and dried over anhydrous potassium carbonate. After filtration, the solvent was removed on a rotary

evaporator yielding 71.2 g (84%) of crude product, which was purified by fractional distillation at 130−135 °C/0.18−0.25 mmHg.18 1H NMR (CDCl3) δ: 2.79 (t, J = 6.0 Hz, 4H), 2.65 (t, J = 6.0 Hz, 4H), 2.58 (t, J = 7.3 Hz, 4H), 1.49 (m, 4H), 1.31 (br, 6H), 0.49 (m, 4H), 0.03 (s, 12H). 13C {1H} NMR (CDCl3) δ: 53.1, 52.7, 41.9, 23.9, 15.8, 0.3 ppm. FTIR (neat): 3366, 3285, 2929, 2877, 2807, 1604, 1495, 1455, 1345, 1301, 1257, 1176, 1127, 1054, 841, 795 cm−1. Tris(3-aminopropyldimethylsiloxy)3-aminopropylsilane (M′3T′, Entry 29). A total of 42.1 g of GAP-0 (0.339 mol M′) was mixed with 25.0 g of 3-aminopropyltriethoxysilane (0.113 mol) and 0.65 g of tetramethylammonium hydroxidepentahydrate. The solution was heated at 60 °C (under N2) for 1 h, and then 6.8 mL of water was added. Heating was then continued to 90−95 °C. A total of 70 mL of toluene was added, and after another 1 h, a vacuum was applied and toluene as well as water and ethanol were stripped off. Once solvent stripping was complete, NMR showed the ethoxy groups to be essentially gone. Heating was continued overnight to ensure that the reaction was at equilibrium, and then the mixture was further heated and stripped as above (i.e., house vacuum, strip up to 165 °C). Upon cooling to room temperature, 53.8 g of material (98.5% yield) was obtained as a light yellow oil. 1H NMR (CDCl3) δ: 2.60 (t, J = 6 Hz, 8H, CH2NH2), 1.39 (m, 8H, CH2CH2CH2), 1.04 (br s, 8H, NH2), 0.46 (m, 8H, CH2Si), from 0.08 to −0.02 (m, 18.5H, CH3Si). 1,5-Bis(3-aminopropyl)-1,1,3,3,5,5-hexamethyltrisiloxane (GAP-1, Entry 25). A total of 20.0 g of GAP-0 (0.0805 mol) was mixed with 6.0 g of D4 (0.0805 mol of D) and 0.15 g of tetramethyl ammonium hydroxide pentahydrate. The mixture was heated to ca. 40 °C under vacuum for 1 h to remove some of the water from the catalyst. Next, a nitrogen atmosphere was established, and the temperature was increased to 90−95 °C and allowed to react overnight. The reaction mixture was then heated to 150 °C for 30 min, and then a vacuum was carefully applied (house vacuum). Heating was then continued to 165 °C, and most volatiles species were stripped off. 2516


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After cooling, ca. 25 g of product (96% yield) was obtained as a light yellow oil. 1H NMR (CDCl3) δ: 2.60 (t, J = 6 Hz, 4H, CH2NH2), 1.39 (m, 4H, CH2CH2CH2), 1.03 (br s, 4H, NH2), 0.45 (m, 4H, CH2Si), from 0.05 to −0.06 (m, 18.6H, CH3Si). 1,3,5-Tris(3-aminopropyl)-1,1,3,5,5-pentamethyltrisiloxane (M′D′M′, Entry 28). A total of 111.8 g of GAP-0 (0.404 mol) were mixed with 77.2 g of 3-aminopropyl-methyldiethoxysilane (0.403 mol) and 1.5 g of tetramethyl ammonium hydroxide pentahydrate. Next, a nitrogen atmosphere was established, and the mixture was heated using an oil bath. As the temperature reached approximately 60 °C, 17 mL of water was added. Heating was continued, and once the temperature reached ∼85−90 °C, 160 mL of toluene was added. After 1 h, vacuum was carefully applied (ca. 40 Torr) and the toluene, excess water, and ethanol were distilled off. Once the volatiles had ceased coming over, the vacuum was broken with nitrogen and the reaction mixture was allowed to remain at 90−95 °C overnight. It was then heated to 150 °C for 30 min to decompose the catalyst, and then vacuum was carefully applied. Heating was continued to an oil bath temperature of 170 °C, during which time volatiles were stripped off. After cooling, ca. 142 g of product (96% yield) was obtained as a light yellow oil. 1H NMR (CDCl3) δ: 2.57 (t, J = 7 Hz, 6H), 1.36 (m, 6H), 1.01 (br s, 6H), 0.41 (m, 6H), from 0.02 to −0.08 (m, 15H).

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PublishedLiteratureDOWCOM/dh_004d/0901b8038004d042. pdf?filepath=ethyleneglycol/pdfs/noreg/612-00004.pdf&fromPage= GetDoc. (c) Wise, H.; Puck, T. T.; Failey, C. F. J. Phys. Colloid Chem. 1950, 54, 734. (5) (a) http://www.qbjohnson.com/p/10365/Default.aspx. (b) Wagner, R.; Modes, G.; Giesen, V. Column for bringing two fluids into contact. WO/2009/147247, Dec 10, 2009. (c) Wuennenberg, W.; Jarausch, H.; Jansen, F.; Wessing, W.; Lorey, M.; Thomas, K. Process and device for drying gas, especially natural gas. DE 19621908 A, April 12, 1997. (6) Manning, F.; Thompson, R. Oil Field Processing of Petroleum; Penwell Publishing Co.: Tulsa, OK, 1991; p 149. (7) (a) Beach, R. K. The Use of Ethylene Glycol Solutions in Heating Systems; National Research Council of Canada: Ottawa, Ontario, Canada, Feb 1963; Technical Note 388. (b) http://msdssearch.dow. com/PublishedLiteratureDOWCOM/dh_004d/0901b8038004d042. pdf?filepath=ethyleneglycol/pdfs/noreg/612-00004.pdf&fromPage= GetDoc; p 26. (8) Bonenfant, D.; Mimeault, M.; Hausler, R. Ind. Eng. Chem. Res. 2007, 46, 8968. (9) Manning, F., Thompson, R. Oil Field Processing of Petroleum; Penwell Publishing Co.: Tulsa, OK, 1991; p 108. (10) (a) Leontiev, A. V.; Rudkevich, D. M. J. Am. Chem. Soc. 2005, 127, 14127. (b) van Dam, M. H. H.; Lamine, A. S.; Roizard, D.; Lochon, P.; Roizard, C. Ind. Eng. Chem. Res. 1997, 36, 4628−4637. (11) The annual production of MEA was 303 000 megatons in 2008. For a review on the production of ethanolamines, see Camara Greiner, E. O. Ethanolamines. CEH Product Review: Chemical Economics Handbook; SRI Consulting: Menlo Park, CA, Jan 2009. (12) http://chemicalland21.com/industrialchem/organic/ TRIISOPROPANOLAMINE.htm. (13) Groszos, S. J.; Day, N. E. Tri-n-propanolamine borate. U.S. Patent 2,942,021 June 21, 1960. (14) Value obtained from nomograph in Silicon Compounds: Silanes & Silicones, 2nd ed.; Gelest, Inc.: Morrisville, PA, 2008; p 592. (15) Lespagnol, A. Bull. Soc. Chim. Fr. 1962, 1117. (16) Mamedov, Sh. Zh. Obshch. Khim. 1963, 33, 3508. (17) Heldebrant, D. J.; Yonker, C. R.; Jessop, P. G.; Phan, L. Energy Environ. Sci. 2008, 1, 487. (18) Dell’Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857.

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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REFERENCES

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CO2 Capture Using Solutions of Alkanolamines and Aminosilicones

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