Proceedings of MARTEC 2010

The International Conference on Marine Technology

11-12 December 2010, BUET, Dhaka, Bangladesh

ROLE OF ACIDS IN THE DEGRADATION OF ALKANOLAMINE DURING CO2

AND H2S REMOVAL PROCESS
Md. Sakinul Islam1*, Rozita Yusoff1, Brahim Si Ali1
1

Department of Chemical Engineering

Faculty of Engineering, University of Malaya
Kuala Lumpur, Malaysia
Email: sakin.chem.buet@gmail.com
ryusoff@um.edu.my
brahim@um.edu.my

ABSTRACT
The formation of organic acid and inorganic acids in CO2 and H2S removal process are common phenomenon.
Amines are basic in nature, which react easily with the acidic components to form heat stable salts and other
degradation products. Heat stable salt and degradation products are problematic in the operation of CO2, H2S
removal unit, as they reduce the solvent capacity to absorb CO2 and H2S, cause corrosion, foaming and solvent
losses. This paper gives an insight on the degradation of amine solvent due to these acidic components and
highlights the latest findings and research work carried out in this area of study.
Keywords: acid; degradation; amine; alkanolamine; absorption; heat stable salt
1. INTRODUCTION
Amines and alkanolamines are widely used in the
natural gas refining for the sweetening of sour gas by
absorbing the CO2 and H2S acidic gases. During the
absorption process amine are highly degraded by this
acidic oxide as a result amine loses its capacity to
absorb these acidic gases. All acidic gases of natural
gas composition play an important role to form amine
to aldehyde and acids. Oxygen directly oxidized the
amine and converted into carbonyl compounds like
aldehyde or ketone or acid compound. Aldehydes
react with water; in aqueous solution of formaldehyde
is hydrated [1]. Aldehydes also react readily with
primary amines. These reactions would not be
significant with tertiary amines. In aqueous solution
of monoethanolamine, formaldehyde will be present
as an equilibrium mixture primarily in the form of
imine with some hydrated aldehyde, carbinolamine,
and aminal. Similar reactions can occur with other
aldehydes such as hydroxyacetaldehyde. The imine
formed from primary or secondary amines such as
MEA may be subject to similar attack by radical
oxidants. The presence of formaldehyde may also
facilitate the oxidation of the amine molecule. Other
less compounds easily hydrated to aldehydes, such as
acetaldehyde and hydroxyacetaldehyde, react at room
temperature with oxygen to produce the
corresponding organic acid [2, 3]. The oxidation
ususally takes place by a free radical chain
mechanism. An initiator extracts a H from the
carbon to produce a free radical. The radical reacts
with O2 to produce a peroxyacid radical. The
peroxyacid radical reacts with aldehyde to propagate
the reaction with the production of the aldehyde

radical and a peroxyacid. So the prevention of amines

loss is the major focus of interest for the chemical
engineer. The prevention of amine losing by acid is
the one of the condition for successful plant operation.
This prevention of amine loss is also the key of
economical benefit. Hence, to identify the
alkanolamines degradations are important. Amine
degradation
compounds
are
quantified
by
chromatographic
methods.
Identification
of
degradation products is performed with several
analytical methods like GC/MS, IC and HPLC etc. In
some cases, synthesis of molecules is necessary to
confirm structure of degradation products. The
highest molecular weight compounds are identified
with a high resolution mass spectrometry technique
(FT-ICR/MS) with electrospray ionization (ESI). In
some cases, NMR analyses are useful to determine
compound structure. Formic, glycolic, acetic and
oxalic acids, nitrite and nitrate are quantified by ion
chromatography. The role of these acids and
degradation path way was critically reviewed and a
brief discussion was given by the following
representation.
2. AMINE BASED ABSORPTION AND
STRIPPING SYSTEM
For over seventy years the alkanolamine process
has been considered the best approach in removing
H 2 S and CO2 for the purpose of purification and
separation. It is based on the reaction between weak
acid (H2S and/or CO2) and weak base (alkanolamines)
to give a water soluble amine acid gas salt. An amine
based sour gas sweetening plant was configured with
absorber and regenerator. The temperature range is

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Proceeedings of MARTE
EC 2010

40-60C annd 100-120C at the absorbeer and the stripper

respectivelly. Mainly amine
a
solventts are used as
absorbentss for sweetenin
ng natural gass and for proloong
use of thiss solvent that is
i transferred to
t the stripper by
means off regenerating
g absorbed gases. Figurre-1
represents a sweetening process
p
of sourr gas.

degradaation productss are ethyleneediamine derivvatives

(THEED
D) [6], which can form wheen CO2, COS or O2
are in an amine system. The basic
b
chemisttry of
degradaation of alkanoolamine is expplained in thee open
literaturre [7] and thesee are given bellow. In the folllowing
chemicaal reaction it iss clear that amiines occur due to the
protonaation and carbaamate formatiion reaction brrought
about byy the hydrolysis of water andd acids.

H+ + OH
H2O
H+ + HS
H2S
HCO
O3 + H+
CO2 + H2O
RNH
H3+
RNH2 + H+
RNH2 + CO2
RN
NHCOO + H+

Amines/Alkanolaminnes + Sour Gas

The same reactionn is also explaiined in the liteerature

[8-10] for DEA deggradation. Theese reactions are
a as
follows. Hydrogen suulfide emittedd hydrogen ionn (Eq.
B.6) in water and caarbon dioxide as well as carrbonyl
sulfide and producess COS and H2S respectivelyy (Eq.
B.7). This
T
reaction causes additioonal reactionss with
DEA molecule.
m

Sww
wet Gas

Natural Gas Com

mponents:
Absorber Chemicals:
CH4, C2H6, C3H8, C4H10, CO
Sweet Gas + DGP
Aminnes/Alkanolamines, Wateer

C5H12, CO2, N2, H2, H2S, O2,

H2O
D
DGP=
Degradation Produccts; = Absorber/ Strippeer Temperature

H+ + HS
H H2S
COS + H2O
CS2 + H2O
CO
OS + H2O
CO2 + H2S
H+ + HCO-3
H2O + CO2

Figure. 1: Typical CO
O2 absorption and
a desorptioon
prrocess [4]
Sour gas components
c
reeact with aminne solvent durring
absorption-desorption cy
ycles graduallly at higher and
a
lower tempperature and some
s
of these reactions (A.11 to
A.11) are given in the following
f
to shhow how DGP
P is
formed [5].
HO-C2H4NH
H2 + HCl
DEA
HO-C2H4NH
H 2 + H 2S
DEA
R-NH2 + O2
MEA + CO22
MEA + COSS
DEA + CO2
DEA + COS
O2
MDEA + CO
DGA + CO2
DGA + COS
DIPA + CO2

HO-C
H 2H4NH3+Cl
HSS
HO-C
H 2H4NH3+HS
HSS
CnH2n+1COOH / Imidazolidonne
OZD, HEI,, HEED
DEA Urea
HEOD, BH
HEEP, THEED
MEA, HEI, BHEED
EG, HMP, DEA, TEA, BHEP
BHEEU
BHEETU
HMPO

B.1
B.2
B.3
B.4
B.5

A.11
A.2
A.33
A.44
A.55
A.66
A.77
A.88
A.99
A.110
A.111

3. BASIC DEGRADATION CHEMIS

STRY
Degraddation products are contaminnants in soluttion
that are deerived from thee breakdown of
o the base am
mine
molecule and
a often causeed reversibly and
a irreversiblyy to
form totallly different chemical speciies. Examples of

B.6
B
B
B.7
B
B.8
B
B.9

DEA molecule directly

d
reactts with CS2 and
successively producees DEA thioccarbamate saltt (Eq.
B.10 & B.11). On thee other hand it produces carbbamate
O2 (Eq. B.13). DEA carbamaate reacts withh MEA
with CO
and DE
EA and forms BHEED
B
and THEED
T
respecctively.
These tw
wo DGP furtheer form BHEI and BHEP witth CO2
respectiively. HEOD is one of the faamiliar DGP off DEA
and thiss is also from DEA carbamaate. Protonatedd DEA
moleculle reacts withh CO2 and converts into MEA,
ethanol and water. Thhe formation of
o MEA is bettter for
DEA syystem because the author assuume that it has better
absorptiion capacity. It
I is also assuume that any amine
system where higher molecular
m
weigght compoundd break
mine like MD
DEA or
down innto lower molecular mass am
DEA to MEA that process willl rich at thee high
absorptiion rate. Alkaanolamines aree oxidized andd form
aldehydde or ketone thhen formed accid. This acid finally
f
forms HSAS.
H
So to protect
p
the form
mation of HSA
AS the
intermeediate reactionn should be controlled at first.
Howeveer there is insufficient innformation inn this
connecttion in the oppen literature. Ethanol can easily
degradee to aldehyde and
a then an accid. This acid forms
various acetate and ester
e
compoundds in amine syystem.
EA are
An oveer view of thee reaction patthways of DE

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Proceeedings of MARTE
EC 2010

to form a salt that is not

n capable of being
b
regeneraated by
the adddition of heat and are thus referred to ass Heat
Stable Salts. Not onlly do they tiee up the aminne and
therebyy reduce the accid gas carryinng capacity, buut they
are alsoo considered corrosive.
c
How
wever, there is still a
consideerable amount of confusion in the industryy over
the terrm Heat Staable Salt. Some
S
propertiies of
common HSS is menttioned in Table -01 below.

mentioned below.

D dithiocarbamate
DEA+CS2 DEA
DEA dithiocarbaamate + DEA DEA dithiocarbamate
d
salt

B.10

DEA + H+

B.12
B.13

DEA + CO2
DEAH+ + CO2

DEAH+
DEACOO-H+
MEA + C2H4OH + CO2

B.11

B.14

DEACOO H + MEA BHEED + COO2 + H2O

B.15

DEACOO-H+ +DDEA THEED + CO2 + H2O

B.16

- +

THEED + CO2

BHEP + CO2 + H2O

DEACOO-H+

HEOD + H2O

Table-001: Common HSS

H in amine system [14]
Name of
mical
Origiin of
Lim
mit
Chem
Formu
HSS
I
Ions
ppm
m
la
anions
Nitratee
NO3
Inorgganic
-

B.17
B.18

Nitritee

NO2

Inorgganic

Formaate

CHO2

Orgaanic

5000

Oxalatte

C2O4

Orgaanic

2500

Acetatte

C2H2O2

Orgaanic

10000

Sulfatee

SO4

Inorgganic

5000

4. ACID FORMATION
F
N REACTION IN AMINE
SYSTEM

Sulfitee

SO3

Inorgganic

5000

Phosphate

PO4

Inorgganic

The reaaction in this sccheme was prooposed to account

for the presence of all th
he anions obserrved in this stuudy.
This acid formation
f
mechanism could be
b applied to any
a
alkanolamiine. Also, it was
w noted that although
a
the acid
a
form of accetic, formic, glycolic, glyooxalic, and oxaalic
acids are shown
s
in the fo
ollowing reactiion, each of thhese
anions are almost complletely ionized to
t the amine heat
h
stable salt in basic solutiions. The literaature [11] cited a
oxidation reaction
r
of ME
EA which are ass follows.

Thiosuulfate

S2O3

Inorgganic

10,000

Thiocyyanate

CNS

Inorgganic

10,000

Glycolate

C2H3O3

Orgaanic

5000

Malonnate

C3H3O3

Orgaanic

5000

Succinnate

C4H5O4

Orgaanic

10000

Chloriide

Cl

Inorgganic

5000

- +

MEACOO H + MEA
BHEED + CO2

HEI + H2O

BHEI + H2O

B.19
B.20

6. SPEC
CIFIC DEGRA
ADATION PRO
ODUCTS BY ACID
A
Whiile Heat Stable Salts (HSS) are common to all
amine solvents, deggradation prooducts are soolventA descriiption of com
mmon
specificc [6, 15-17]..
degradaation productss found in various
v
gas trreating
solventss follows.

5. TYPICA
AL HSS IN AM
MINE SYSTE
EM
Heat sttable salt (HSS
S) formation iss another form
m of
active amiine loss. The amine
a
and an acid form a salt
s
that cannoot be regeneraated in the stripper [12, 13].
1
Strong acidd anions such as formate, accetate, thiosulfaate,
thiocyanatee, and chloridee can tie up ann amine moleccule

mides
Formam
N-foormyl aminess (formamides) are degraadation
productts generally foound in gas treeating solutionns that
are baseed on primary and secondaryy amines [18]. Under
certain conditions all primary andd secondary amines
a
react with
w the formic acid in solutioon (via dehydrration)
to form
m n-formyl amines.
a
The data from process
p
solutionns containing formate
f
as a HSS
H anion show
w that
the following equilibbrium relationnship exists in
i the
solutionn between thee formate HSS
S and the n-fformyl
MEA (M
MEA-F) [19].
Form
mic Acid + ME
EA MEA-F + Water
Since thhe above equaation represennts equilibrium
m, it is
also possible to hydroolyze MEA-F back into ME
EA and

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Proceedings of MARTEC 2010

formic acid. The heat and water present in the stripper

of the amine unit will generate a new equilibrium if
removing one of the above components disturbs the
balance of the equation.
HEED
HEED is a degradation product of MEA from
reactions with CO2. There is a wealth of literature on the
reaction mechanisms and the corrosive nature of HEED
[20]. While much of the literature has focused on MEA
in CO2 service only, HEED has been found in many
combined systems treating H2S and CO2.
HEEU
HEEU is a degradation product of MEA that is not
that well known since most of the literature has focused
on degradation in CO2 service. HEEU is formed via the
same reaction pathway as HEED when COS is present
in the gas [21].
Polymers
We generally find polymers when HEED, is present
in MEA systems treating H2S and CO2. These polymers
are formed from the reaction of HEED with MEA
molecules to make longer chained ethylenediamines
[22]. We also find polymers when THEED is present in
DEA systems treating H2S and CO2 [22].
BHEEU
BHEEU is an inert degradation product of DGA
which formed in the presence of COS and CO2 [21].
.Formation of BHEEU can be reversed by thermal
reclaiming.
Morpholine
This is an inert degradation product of DGA that,
while rare, can occur when the solution is subjected to
high temperatures.
THEED
THEED is a well-known degradation product of
DEA from reactions with CO2. There is a wealth of
literature on the reaction mechanisms and the corrosive
nature of THEED [20, 21]. While much of the literature
has focused on DEA in CO2 service only, THEED has
been found in combined systems treating H2S and CO2.
Bis-HEP
Bis-hydroxyethyl piperazine (Bis-HEP) is a wellknown degradation product of DEA from reactions with
CO2. There is a wealth of literature on the reaction
mechanisms of bis-HEP [20, 21]. While much of the
literature has focused on DEA in CO2 service only, bisHEP has been found in combined systems treating H2S
and CO2.

MEA
In the presence of certain chemical compounds
(oxygen) or intermediates, it is possible to degrade or
break down the DEA molecule to simpler amines.
Monoethanolamine (MEA) is one of the simpler amines
that may be formed from DEA degradation. It is
important to monitor the level of MEA in the circulating
DEA system due to Amine Stress Corrosion Cracking
(ASSC) concerns associated with MEA. MEA will also
generally further degrade in the system.
Bicine
Bis-(hydroxyethyl) glycine (Bicine) is a degradation
product formed in the presence of DEA and unstable
chemical intermediates, and is considered corrosive [23,
24].
DIPA-OX
Hydroxypropylmethyloxazolidone (HPMO or DIPAOX) is a well-known degradation product of DIPA from
reactions with CO2. There is a wealth of literature on the
reaction mechanism of DIPA-OX [20, 21, 25]. The
literature also states that DIPA-OX is the endpoint of
DIPA degradation in CO2 service (due to steric
hindrance), so polymers of DIPA are not supposed to be
formed like they are with MEA and DEA.
MDEA Fragments
MDEA in Tail Gas Treating units (TGTU), Acid Gas
Enrichment units (AGE), and in some main amine
systems should be monitored for MDEA fragments.
These include MMEA, DEA, Bicine and C2+ HSS
anions [26]. It is also important to note that as
ethanolamines (from MDEA degradation) accumulate in
the solvent, they will generally undergo further
degradation to compounds listed in the above sections.
The presence of these primary and secondary amines
may affect the gas treating selectivity of the amine
solution.
Dimers
The literature states that steric hindrance prevents
further degradation of DIPA-OX to diamines
(dimers). However, we generally do find dimers in
Sulfinol-D systems treating H2S and CO2. These
dimers are similar to the diamines found in MEA and
DEA systems, and are likely formed via the same
pathway.
TIPA
TIPA may be found in systems treating H2S and CO2
utilizing Sulfinol-D, when evidence of oxygen
degradation is present. Literature shows that when
amines degrade they generally form simpler amines, but
sometimes these simpler amines react with the base
amine molecule (or others) to form a more complex
amine [27].

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Proceeedings of MARTE
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7. COMMO
ON DEGRADAT
TION PRODUCTS AND EFFEC
CT
All alkkanolamine deg
gradation produucts are not saame
in behavior, some of these are acidic and
a some of thhese
are alkalinne based. Dep
pending on thhe nature of the
degradationn products thesse are classifieed as follows.
7.1 Acidic degradation product
p
Acidic degradation prroducts are higghly corrosive for
plant unit, thus metallic unit
u of the gas sweetening pllant
is highly interactive by
y this product. So the aciidic
degradationn products are
a
very harm
mful among all
degradationn products. Heeat stable saltss are the comm
mon
degradationn products off amine strippping system and
a
these are potentially co
orrosive. All of these aminnes
degraded and
a formed caarboxylic acidss. These acids are
capable of
o causing fu
urther chemicaal reaction with
w
miscellaneeous degradatio
on products. Byy this reaction the
concentratiion of contam
minants increaases continuouusly
during abssorption-desorp
ption cycles and finally shoows
operational problems.
d
product
p
7.2 Basic degradation
The alkkaline degradaation products are
a less corrossive
than acidicc or some of these
t
are noncoorrosive but both
still have a bad impact on plant operaation or even the
neutral DG
GP has the sam
me effect too.. It increases the
viscosity and
a as a resultt it highly inhhibits the soluttion
flow rate. This lower flow rate shhould affect the
efficiency of the plant [28]. To accelerate the pllant
lower flow
w rate to satisfactory flow rate,
r
high enerrgy
consumptioon is required. For this reasoon no degradattion
products arre expected.
d
prroduct
7.3 Ionic degradation
The deegradation product which coontains chargee at
the chain end
e and it may
y be positive or negative thhese
are definedd as ionic degrradation produccts. The literatture
is citied itss effect on thee plant perform
mance [8, 29, 30].
3
Ionic degrradation produccts are more porn
p
to affect the
plant perfoormance becau
use it is easilly react with the
componentts and form miiscellaneous reaction productts.
7.4 Polymeric degradatiion product
Many articles refleect a lot of information on
polymeric degradation products but there is no speciific
polymer formation deegradation reeaction [31-333].
Polymeric degradation products
p
identtified by GC-M
MS
detection may be neutrral or living. Living polym
mer
means it coontains a functtional group at the chain endss of
the moleccule which arre capable off causing furtther
chemical reaction with accidic oxide or any reactive unnit.
The literaature cited very inadequuate informattion
regarding the polymerization reacttion mechaniism
though it has a satisfaactory detectioon report. Wide
W
ranges off research on
n polymerizatiion reaction are

suggestted to recover this literaturee gap. Literatuure [7]

focusedd that THEED
D, Bicine, HSS,
H
HE-Sarccocine,
HEED, HEOD, BHE
EED and TH
HEED are corrrosive
compouunds [31, 34]. Actually these
t
are corrrosive
becausee all of these are acidic orr basic or conntain a
living functional
fu
grouup or oxazolidoone ring at thee chain
end or in
i its structure.
utral Degradation product
7.5 Neu
Neuutral degradatiion products having no active
functionnal group are very harmfull for fouling effect.
These degradation
d
products are inaactive and just move
towardss the entire sollution direction. It also makkes the
solutionn more viscouus. Neutral degradation prooducts
having no movementt so there is a great probabiility to
adherinng with plant pipelines, as a result that place
easily corrode
c
or desstroy. Carl andd Haws studieed the
effect of neutral degraadation productts [35]
7.6 Volaatile degradattion product
Volaatile degradatioon products arre highly harm
mful to
the envvironment. Geenerally these gases cause green
house effect,
e
world climate changge and so onn. The
effects of the aminne were well conducted in
i the
literaturre [36] last yeaar.
mmon effect of
o DGP
7.7 Com
The foaming behaavior of degradation productts was
conductted by Thitaakamol and Veawab [30,, 37].
Corrosion behavior of degradatiion products were
conductted by Dawoodu and Meiisen [31] andd also
conductted by the reseearchers [34, 366]. The recent article
[34] poiinted out severral problems which
w
occurred due to
irreverssible degradatioon reaction andd mentioned beelow.
Reductionsolutio
oncapacityandp
plant
performance
Foamingeffectofdegradationproducts

Capital/MaterialofConstructionIsssues
Corrosioneffectofdegradation
products

Environmentaleffectof
degradationproducts.
Foulingeffecto
ofdegradation
products

NCLUSION
8. CON
Durring the sour gas sweeteninng process a lot of
solvent are losses by amine degradation. The

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Proceedings of MARTEC 2010

degradation products arises various difficulties and as a

result the remediation of this problem has become a
major focus of interest for the last few decades. HSAS
neutralization
techniques
(vacuum
distillation,
electrodialysis, ion exchanges) are still being developed
to improve plant efficiencies and reduce operation
problems.

THEED

The literature mostly cited the heat stable salt and its
minimization. HSAS are basically the reaction products
of acid and amine. Amine is the main solvent; on the
other hand an acid is the by product, if we control the
acid formation in amine system then automatically
reduces the HSAS formation. Acids can also be
converted to acid amides by adding some additives.
Because amides contain CONH2 functional group this is
capable to capture more acid gases. So we need further
research on it to recover the research gap. The author
suggested the acid remediation by converting into
amides compound. Author also would like to put
emphasis for the minimization of the acidic content
inside the solution. The above mentioned contents of
this review paper highlighted very important and recent
information regarding alkanolamines degradation by
acid. Knowledge of the reaction mechanism aids the
development of procedures to minimize degradation or
purify partially degraded solutions. Therefore, the
overall representation would help to understand the role
of both inorganic and organic acid on amine
degradation.

HPLC

BHEI
BHEEU
NMR
GC-MS

IC
FTIR
HPLC-RID

REFERENCES
[1]

[2]

[3]

ACKNOWLEDGEMENT
The authors would like to acknowledge Ministry of
Science, Technology and Innovation (MOSTI),
Malaysia, for the project: RG003/09AET and the
University of Malaya for the financial support and for
providing us with an excellent research environment.

[4]
[5]
[6]

ABBREVIATIONS
NG
DIPA
DEA
MDEA
MEA
DGP
DGA
HSS
HSAS
AMP
HEP
BHEED
BHEP
HEOD

Natural gas
Di-isopropanolamine
Diethanolamine
Methyldiethanolamine
Monoethanolamine
Degradation product
Diglycolamine
Heat stable salts
Heat stable amine salts
Aminomethyl propanol
Hydroxyethyl piperazine
N,N-Bis(hydroxyethyl) ethylnediamine
N,N-Bis(hydroxyethyl)-piperazine
Hydroxyethyl-oxazolidone

N,N,N-Tris(hydroxyethyl)ethylenediamine
N,N Bis (hydroxyethyl)imidazolidone
N,N-Bis(hydroxyethoxy-ethyl)urea
Nuclear magnetic resonance
Gas chromatography mass
spectrometer
High performance liquid
chromatography
Ion chromatography
Fourier transforms infrared resonance
spectrometer
High performance liquid
chromatography-refractive index
detector

[7]

[8]

[9]

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