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Development of an Energy-efficient CO2 Capture Process Using

Thermomorphic Biphasic Solvents

Article  in  Energy Procedia · December 2013

DOI: 10.1016/j.egypro.2013.05.224

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Energy Procedia 37 (2013) 1254 – 1261

GHGT-11

Development of an energy-efficient CO2 capture process

using thermomorphic biphasic solvents
Jiafei Zhanga,b, Yu Qiaob, Wanzhong Wangb, Robert Mischb, Khuram Hussainb,
David W. Agarb *
a
Department of Chemical Engineering, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom
b
Department of Biochemical and Chemical Engineering, Technical University of Dortmund, D-44227 Dortmund, Germany

Abstract

A novel CO2 capture system using thermomorphic biphasic solvent (TBS) has been studied in this work. It exhibits a
thermal-induced liquid-liquid phase separation (LLPS) behaviour, which intensifies CO2 desorption at temperature of
80 °C and therefore enables using low value heat ca. 90 °C to reduce the process operating cost. To regulate the phase
change behaviour, blended amine solvents were formulated for attaining a homogeneous solution in absorption and
biphasic system in regeneration. Thermal and oxidative degradations were also surveyed for the selected amines and
the degradation products were analysed by gas chromatography - mass spectrometry (GC-MS). A bench-scale unit
with a glass column of 40 mm inner diameter and random packings of 1 m height was employed for measuring the
pressure drop and liquid hold-up as well as other physicochemical properties to assess the technical feasibility of such
novel system.

2013The
© 2013 TheAuthors.
Authors.Published
Publishedbyby Elsevier
Elsevier Ltd.Ltd.
Selection
Selectionand/or
and/orpeer-review
peer-reviewunder responsibility
under of GHGT
responsibility of GHGT

Keywords: absorption; biphasic solvent; novel system; phase change; degradation; wettability

1. Introduction

Anthropogenic CO2 emission from fossil fuels combustion is considered to be one of the main causes
of global warming. In order to mitigate the climate change, strategies such as improvement of energy
efficiency, development of low CO2 sources of energy and deployment of CO2 Capture & Storage (CCS)
technologies are proposed for reducing the greenhouse gas emission [1]. Due to reconcilement of the
fossil fuels use, CCS including capture, transport and storage is one of the most valuable technologies for

* Corresponding author. Tel.: + 49-231-755-2697; fax: +49-231-755-2698.

E-mail address: [email protected].

1876-6102 © 2013 The Authors. Published by Elsevier Ltd.

Selection and/or peer-review under responsibility of GHGT
doi:10.1016/j.egypro.2013.05.224
 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261 1255

emission reduction [2]. Because of low CO2 partial pressure in post-combustion capture (PCC) process,
chemical absorption is favoured to achieve high loading capacity, but high energy consumption for
solvent thermal regeneration is the major shortcoming and solvent degradation also becomes a notable
challenge since other contaminant gases such as O2, SOx and NOx are present in flue gases.
Amine scrubbing is presently both the preferred option and probably the only commercially mature
technology for CO2 removal. However, it has been estimated that the desorption step would be
responsible for more than half of the overall processing costs, primarily due to the high energy
consumption for the solvent regeneration [3]. Monoethanolamine (MEA) is the most commonly used
solvent for CO2 absorption [4], but it reveals several weaknesses: (a) low net CO2 loading capacity, (b)
solvent degradation, (c) corrosion and (d) high energy consumption.
Many researchers have thus focused on searching new absorbents and systems for CO2 capture with
following criteria: (i) low energy requirement, (ii) high reactivity and capacity with respect to CO2, (iii)
minor environment impact, (iv) low degradability and corrodibility. The French Institute of Petroleum
(IFP) invested a DMXTM process with a preheated decantation unit to split the two liquid phases before
stripping [5]. Svendsen et al. also focused to develop absorbent systems that forms two liquid phases by
cooling after CO2 loading, where one of the phases is CO2 lean, can directly be recycled to absorber and
another has a very high concentration of CO2, thereby having a potential for low circulation rate and more
energy efficient CO2 desorption [6]. Besides, Hu investigated a elf- phase transitional
absorption process using partially miscible organic solvents such as alamine as activated component and
alcohol, e.g. isooctanol, as extractive agent to reduce the energy requirement [7].
Biphasic solvent, for example lipophilic amines N,N-dimethylcyclohexylamine (DMCA) and
dipropylamine (DPA), was initially proposed by Agar et al. to cut the regeneration temperature down to
80 °C or even lower, enabling the utilisation of low value or even waste heat for regeneration purposes
[8,9] lipophilic -induced miscibility gap
arises upon modest heating of the loaded solvent in the temperature range of 60-80 °C. The previous study
has successfully identified suitable lipophilic amines for CO2 absorption by a series of screening tests
[10]. The selected amines were classified into two categories: absorption activator and regeneration
promoter. In order to achieve desired ab-/desorption characteristics, blended solvent comprising activator
and promoter were proposed for the energy-efficient CO2 capture process. In comparison to conventional
alkanolamines such as MEA, the novel TBS system has exhibits several advantages, for instance, (i) high
net CO2 capacity, (ii) low required regeneration temperature, (iii) enhanced solvent regeneration, (iv)
moderate energy consumption and (v) satisfactory chemical stability. However, further studies on the
regulation of solvent phase change, identification of degradation products and packing wettabilities in
absorption column should be conducted so as to deep inspect the performance of the novel TBS system.

2. Formulation of TBS absorbent

2.1. Phase change behaviour

According to the screening test, activator N-methylcyclohexylamine (MCA) and promoter DMCA
were picked out as promising candidates for CO2 absorption. Due to the limited aqueous solubility of
lipophilic amines, addition of foreign solubiliser was considered to regulate the phase change behaviour.
Various organic solvents such as non-volatile alkanol 1,4-butanediol and 2-ethyl-1-hexanol, tertiary amine
N-methyl-diethanolamine (MDEA), sterically hindered amine 2-amino-2-methyl-1-propanol (AMP) and
2-amino-2-methyl-1,3-propandiol as well as diamine piperazine and N,N-dimethyl-1,3-propyl-diamine
were screened in the experiment. AMP with its remarkable performance on significant increase of critical
solution temperature as well as restricted negative influence on absorption and regeneration was
1256 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261

recommended. As seen from Fig. 1, increase the proportion of MCA can enhance the phase change
temperature. Nevertheless, the lower critical solution temperature (LCST) and liquid phase separation
temperature (LPST) are still lower than 30 °C in the 4M binary blended solution. Addition of solubiliser
AMP can dramatically improve it: most of the prepared solutions achieve the LCST over room
temperature as presented in Table 1 and the ternary TBS solutions comprising 3M DMCA + 1M MCA
with additional AMP (1-1.5M) were thus selected to obtain a homogeneous absorbent for CO2 scrubbing.

35
Table 1. LCST of blended TBS solutions
Solution: 4M DMCA+MCA
30
LCST Total Amine LCST
LPST Conc.
25 DMCA MCA AMP
Temperature ( C)

mol/L mol/L mol/L mol/L °C

o

20
5 3 1 1 31-32
15
5.25 3 1 1.25 43-44
10 5.5 3 1 1.5 50-52
5 4.5 2.7 0.9 0.9 26-27
4.75 2.7 1.35 0.9 35-36
0
0:4 1:3 1:2 1:1 2:1 3:1 4:0 4.25 2.25 1.35 0.9 28-29
Composition
4 2 1 1 <20
Fig. 1. LCST and LPST for DMCA+MCA solution

2.2. Absorption and desorption

Screening tests on foreign solubilisers indicated that additional alkanol slightly increased the reaction
rate of absorbing CO2 into amine solution but exhibited negative influence on solvent regeneration since it
inhibits the LLPS and increases the phase change temperature for rich solvent; tertiary amine is not so
favoured because it decreased the absorption rate and CO2 capacity; diamine significantly enhanced the
CO2 rich loading however reduced the regenerability; sterically hindered amine showed a positive effect
on CO2 loading capacity nevertheless the proportion of solubiliser must be restricted no more than 15wt%
so as to limit the negative influence on LLPS and regeneration.
According to the overall performance, AMP was selected as a promising foreign solubiliser for the
further study. Therefore, a ternary aqueous blended solvent DMCA+MCA+AMP (TBS-3) was employed
in this work. Alternative absorbents with different component proportions were tested to observe the ab-
/desorption characteristics and phase change behaviours. For maintenance of the favourable regenerability
and low desorption temperature, DMCA was remained as the major component; minor MCA was used to
accelerate CO2 absorption; additional AMP was applied to enhance the LCST of lean solvent to 30-40 °C.
A comparison of ternary aqueous blended solvents with varying proportions was experimentally
investigated according to the solvent formulations listed in Table 1. There is no significant difference on
net CO2 loading among those solutions when the concentration is over 4.5 M. In comparison to MEA, the
net loading of such TBS-3 absorbent achieves > 3.5 mol/kg, which is more than 150% higher than
benchmark 30wt% MEA solution.

3. Solvent degradation

Solvent loss is one of the noteworthy challenges in the amine based PCC process. It is contributed by
solvent vaporisation, foaming, thermal degradation and oxidation. Compared to alkanolamine, volatility
 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261 1257

loss of lipophilic amine is more serious, principally due to its lower aqueous miscibility. However, such
physical loss can be recovered by a subsequent scrubbing unit [8]. Foaming was also observed in the
DMCA based solvent, but it can be controlled by optimising the operation conditions and using addtional
defoaming technologies. Due to the moderate operation temperature required for desorption, thermal
degradation is negligible in TBS system. The oxidative degradation of lipophilic amines was also lower
than that for primary and secondary alkanolamines. In order to explore the degradation products and
mechanism for the novel TBS absorbents, intensive conditions such as high O2 partial pressure and
elevated temperature were used to enhance solvent oxidation.
Table 2. Main thermal degradation products

60 Total amine loss (left) 6 Amine Compounds

Heat stable salts (right)
50 5
MEA
Total amine losses (%)

Heat stable salts (%)

40 4
1-(2-hydroxyethyl)- N-(2-hydroxyethyl)-
30 3 2-imidazolidone ethylenediamine

20 2 AMP

10 1
3,4,4-trimethyl-2- 4,4-dimethyl-2-
oxazolidinone oxazolidinone
0 0
MEA w/o CO2 AMP DMCA MEA MCA
HO

Fig. 2. Solvent thermal degradation after 6 weeks N

H
2-methylamino-2- 4,4-dimethyl-2-
Oxazolidinones Formation methyl-1-propanol imidazolidinone
ethylcyclo
DMCA MCA
hexylamine
(1)
MCA cyclohexylamine DMCA
N-methyl dicyclohexylamine
Demethylation / Methylation Reactions

(2)

3.1. Thermal degradation

The investigation of thermal degradation for biphasic solvents was conducted in 20 ml glass test tubes
with 10 ml CO2-saturated amine solution for each at 120 °C for 6-8 weeks. It is unfair for lipophilic
amines to be treated at such high temperature, but the reaction is thus accelerated and the thermal
degradation products can thus be determined. Before analysis, the solution was treated with 15% CO2, so
that the results can be compared with those in the Vapour-Liquid-Equilibrium (VLE) test. The samples
were analysed by acid-base titration to ascertain total amine losses, by Shell Method Series to determine
1258 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261

the amount of Heat Stable Salts (HSS) and by GC-MS (HP 5973) to identify volatile oxidation products.
Fig. 2 presents the total amine loss after a 6-week thermal degradation test. CO2 is proved to take a
dominant role to induce thermal degradation, MCA is unstable at high temperature and DMCA performs
much better than the benchmark solvent MEA. Table 2 shows the main degradation components at 2 bar
and a thermal condition in presence of CO2. The thermal degradation mechanisms of MEA such as
oxazolidone and imidazolidone formations were well studied by Davis [11]. The CO2 involved
oxazolidinone formation (Eq. 1) is the major degradation reaction for AMP, while demethylation and
methylation (Eq. 2) are the main reactions for lipophilic amines MCA and DMCA. The thermal
degradation shifts a lipophilic amine to other amines which are still active to react with CO2 and also have
the capability to be regenerated as well as recycled for absorption.

3.2. Oxidative degradation

The oxidative degradation experiment was carried out in a 300 mL glass bubble column containing 200
mL amine solution at 50 °C with 2 mL/min CO2 and 98 mL/min O2. The intensified condition such as
high O2 partial pressure was applied for reducing the reaction time. In order to minimise the influence of
solvent vaporisation, chilled water at 10 °C was used in condenser and a control experiment with N2 in
place of O2 was also performed for the purposes of comparison and to distinguish oxidative degradation
from other losses. The samples were taken with an interval of 2 days for observing the total amine losses.
After completion of the degassed, sampled and analysed
by the same method that used for thermal degradation.

Table 3. Main oxidation products of MEA and AMP

6
MW w/o Fe(II/III)
Amine Component Structure w/ Fe(II/III)
(g/mol) 5
Heat stable salts (%)

MEA N-methyl 4
59.07
formamide
3

oxazolidin-2-one 87.08 2

1
AMP 2-methylamino-2-
103.16 See Table 2
methyl-1-propanol
0
4,4-dimethyl-2- AMP Blend DMCA MEA MCA
115.13 See Table 2
oxazolidinone
Fig. 3. Heat stable salts in oxidative degradation

HHS are the most harmful products formed in oxidative degradation, they represent the extent of amine
degradation. Fig. 3 illustrates that the blended solvent DMCA+MCA+AMP (3+1+1M) and DMCA have
good chemical stabilities against oxidation, while MCA significantly degrades and forms HHS in presence
of O2. The mechanisms of MEA oxidative degradation has already been elucidated by Goff [12]. As seen
in Table 3, N-methylformamide and oxazolidin-2-one are the most abundant degradation products from
MEA solution. Those components are inactive for CO2 absorption. Compared to MEA, the oxidative
degradation of AMP is much more insignificant. Due to different molecular structure, the degradation
products of lipophilic amines are quite distinctive from alkanolamines. Thereby, cyclohexanone and
cyclohexanone oxime were determined as the most considerable oxidation components according to Eq. 3
& 4. The other trace components are lipophilic amine via dealkylation and alkylation by shifting a -CH3 or
-C6H11 group as elucidated in Eq. 2. No oxidised product was observed in DMCA solutions. Dealkylation
 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261 1259

and alkylation are the major reaction in the oxidative degradation experiment and the main products are
reformed lipophilic amines and still active for CO2 absorption. It proves that DMCA is a chemically stable
component and is hence recommended as a major composition used in the TBS system.

Ketone formation: (3)

Oxime formation: (4)

4. Packing wettability test

The bench-scale experiment was performed in a glass column of 0.04 m inner diameter with a 1 m
random packing at 30 °C and atmospheric pressure. The packings consisted of 3, 5 6 or 8 mm Raschig
rings and various materials such as ceramic, plastic or metal with the bed porosity of 0.36-0.88. Water,
MEA, MCA and TBS-3 solutions were used as the liquid phase. The liquid surface tensions were varied
from 0.028 to 0.075 N/m for viscosities of 1-30 mPa s. The gas and liquid mass flow rates applied ranged
from 10 to 75 L/min containing 15 mol% CO2 and 60 to 200 mL/min comprising 4.5-5.5M amine,
respectively. Gas flow rates were measured by a BronkhorstTM EL-FLOW controllers and liquid flow
rates by Peltonturbine flowmeter (Flo-Sensor 101, McMillan). Liquid leaving the column outlet at the
bottom of absorber was collected and weighed on a balance (Sartorius 3862) for calculating the total
liquid hold-up. The pressure drops through the packed bed were measured with a differential pressure
transducers (HBM PD1) connected at different positions between the top and bottom of the column.

4.1. Pressure drop

In comparison to MEA solution, biphasic solvent has created higher pressure drop at the same
experimental conditions. It is primarily due to the higher viscosity of the lipophilic amine solution. The
pressure drop of blended solvent DMCA+MCA+AMP (3+1+1.5M) is even higher than MCA solution
owing to the viscous aqueous solution of DMCA. The influence of CO2 loadings on pressure drop was
also investigated: it was relative low when the unloaded solvent ( = 0 mol/L) was used at the 1st run; then
significantly increased when lean solvent ( 0.12 mol/L) was applied at the 2nd run; and even higher
when the rich solvent ( 0.2 mol/L) was employed. This is mainly as a result of the viscosity
enhancement by dissolving CO2 into amine solvent. On account of viscosity-induced effect on pressure
drop for biphasic solvent, higher porosity packings are suggested to be applied to reduce the pressure drop
and to eliminate the negative influence. As illustrated in Fig. 4, by increasing the diameter of metal
Raschig ring (RR-i-M), the pressure drop is prominently decreased. Increase of packing porosity can also
obtain a large operation range, because the flooding point was found at F-factor of 0.3 Pa0.5 for 6 mm
Raschig ring, while it was observed at F-factor of 0.35 Pa0.5 for 8 mm Raschig ring.

4.2. Liquid hold-up

The total liquid hold-up (hL) was measured in experiment. It is mainly dependent upon the physical
properties of packings and the specific liquid load. hL of the ceramic rings has exhibited higher values
than those of the metal and plastic rings, which is mainly due to the roughness of the packing surface. It
was also increased by raising gas and liquid velocities. Biphasic solvent performs a higher hL value
compared to MEA and the CO2 loading also has a positive influence on hL.
1260 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261

4.3. Physicochemical properties

The density ( ) of amine solvents was measured by varying temperatures (30-80 °C) and CO2 loadings
(0-2.5 mol/L). Temperatures have a negative influence on density but CO2 loadings show a positive linear
influence in amine solutions since the effect of CO2 dissolution into aqueous solution on liquid volume is
negligible. The tendency of lipophilic amine is the same as alkanolamine. Both the values for lean and
rich solvent, =0.92 g/ml at 0 mol/L and = 1.03 g/ml at 2.5 mol/L, are feasible for column
operation.
The viscosity ( ) was determined by capillary Ubbelohde Viskosimeter (Schott) from 25 °C to 60 °C.
The values measured are in the order of MEA > MCA > Water for pure amines, but MCA+Water >
MEA+Water > Water for the lean solutions. The particularly behaviour was found in the MCA solution,
because the viscosity of MCA+Water is higher than both pure MCA and water. This can be explained by
the interaction of the molecules, especially, the reformation of the hydrogen bonding between MCA and
water prolongs the molecular chains. Moreover, the viscosity can be increased by CO2 loading after
absorption and values for loaded MCA solution ( = -3 ( =
higher than for MEA ( = 3.3 m 2.5 mol/L and 30 °C, which becomes a challenge for the
pump and piping system.
The surface tension was measured by bubble pressure method at 25-60 °C. The surveyed values of the
lean solutions are in the order of Water > MEA > MCA. The lower surface tension has important
influence on the mass transfer and it becomes another advantage of lipophilic amine. The surface tension
of the solutions is decreased by temperature increasing and increased by CO2 dissolved.
Contact angle ( ) is a quantitative measure of the wetting of a solid by a liquid. It is defined
geometrically as the angle formed by a liquid at the three phase boundary where a liquid, gas and solid
intersect. A low value of indicates that the liquid spreads, or wets well, while a high contact angle
indicates poor wetting. If < 90°, the liquid is wet the solid; if > 90°, it is non-wetting; and a zero
contact angle represents complete wetting. The values for lipophilic amine on the tested materials prove it
more wettable than alkanolamine.

5. Novel TBS process

In order to intensify CO2 regeneration from the loaded solvent, improved methods such as agitation,
nucleation and phase split were employed. In the regeneration (see Fig. 5), a continuous stirred-tank
reactor (CSTR) was used for desorption process in place of conventional steam stripping and porous
particles was placed in the phase separator before feeding to regenerator so as to accelerate CO2 release by
nucleation. According to the experimental results and thermodynamic calculations [9], the energy
consumption of TBS process is only less than 2.0 GJ/t-CO2, which is reduced by over 50% in comparison
to conventional MEA-based technology. The excellent performance of TBS absorbent makes it the most
promising alternative solvent for the new generation PCC technology and the low-cost TBS process
demonstrates significant potential for accessing the technical viability in the future scale-up study.

6. Conclusions

For ameliorating the challenges occurred in the previous study on lipophilic amines, a new ternary
blended solvent DMCA+MCA+AMP was formulated and selected by screening tests. The TBS-3
absorbent has successfully met the desired phase change temperatures, remained a high net CO2 loading
and exhibited a remarkable chemical stability against degradation. The technical feasibility of using TBS
 Jiafei Zhang et al. / Energy Procedia 37 (2013) 1254 – 1261 1261

absorbents were also studied in the bench-scale unit. Compared to MEA, the lower values for density,
surface tension and contact angle of biphasic solvent on various packing materials demonstrate the
favourable technical feasibility, but the higher values for viscosity of rich solvent, pressure drop and
liquid hold-up indicate the design and modification of convention absorption column are required.
3000

RR-5-M [1]* * [1] 1st Run

RR-5-M [2] [2] 2nd Run Treated Gas CO2
RR-5-M [3] CO2 to Storage Compressor
2500
RR-6-M [1]
Water (in)
RR-8-M [1] Washing
RR-6-P [1] Section
RR-6-P [2] Condenser
Specific pressure drop (Pa/m)

2000 Water (out)

Lean Solvent CO2

Pump
Cooler
1500
HEX

Lean Org. Solvent

1000 80 °C
Absorber Pump

500 HEX Nucleation Hot Stream (in)

Agitation
60 °C
Raw Gas
Pump Regenerator
Phase
Rich Solvent

0
0,24 0,26 0,28 0,30 0,32 0,34 0,36 Rich Aq. Solvent
Gas Load F-factor (Pa )
0.5 Separator
Hot Stream (out)
Lean Aq. Solvent Pump
Pump
Fig. 4. Pressure drop with blended
TBS-3 solution Fig. 5. TBS process flow sheet with phase split

Acknowledgements

This work is a part of the Ph.D. thesis of J. Zhang supported by Shell Global Solutions International B.V.

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